CN103965129B - Prepare the method for 3-(2-hydroxyethyl)-2-oxazolidone - Google Patents
Prepare the method for 3-(2-hydroxyethyl)-2-oxazolidone Download PDFInfo
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- CN103965129B CN103965129B CN201410195364.XA CN201410195364A CN103965129B CN 103965129 B CN103965129 B CN 103965129B CN 201410195364 A CN201410195364 A CN 201410195364A CN 103965129 B CN103965129 B CN 103965129B
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- hydroxyethyl
- oxazolidone
- ethyleneimine
- compound
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- 238000000034 method Methods 0.000 title claims abstract description 24
- QBGJZIGMETUVBL-UHFFFAOYSA-N 3-(2-hydroxyethyl)-1,3-oxazolidin-2-id-4-one Chemical compound OCCN1[CH-]OCC1=O QBGJZIGMETUVBL-UHFFFAOYSA-N 0.000 title abstract description 40
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract description 10
- -1 nitrogenous compound Chemical class 0.000 claims abstract description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 7
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 7
- JAYRGGYYLFXBOK-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2H-1,3-oxazol-2-id-4-one Chemical compound OCCC1C(N=[C-]O1)=O JAYRGGYYLFXBOK-UHFFFAOYSA-N 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 229910001220 stainless steel Inorganic materials 0.000 claims description 36
- 239000010935 stainless steel Substances 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 235000021050 feed intake Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 abstract description 10
- 239000003054 catalyst Substances 0.000 abstract description 7
- 239000002184 metal Substances 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052755 nonmetal Inorganic materials 0.000 abstract 1
- 235000011089 carbon dioxide Nutrition 0.000 description 42
- 239000000047 product Substances 0.000 description 37
- 238000009413 insulation Methods 0.000 description 34
- 238000003756 stirring Methods 0.000 description 34
- 238000013022 venting Methods 0.000 description 34
- VYONOYYDEFODAJ-UHFFFAOYSA-N 2-(1-Aziridinyl)ethanol Chemical compound OCCN1CC1 VYONOYYDEFODAJ-UHFFFAOYSA-N 0.000 description 33
- 230000005311 nuclear magnetism Effects 0.000 description 32
- 230000002194 synthesizing effect Effects 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 239000004593 Epoxy Chemical class 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 208000001408 Carbon monoxide poisoning Diseases 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000012867 bioactive agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 description 1
- 229960003907 linezolid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention discloses the method that one prepares 3-(2-hydroxyethyl)-2-oxazolidone.The method, comprise the steps: under the condition of nitrogenous compound as catalyzer, the 1-of compound shown in formula II (2-hydroxyethyl) ethyleneimine is carried out cyclization in carbon dioxide atmosphere, reacts complete and obtain compound 3-shown in described formula I (2-hydroxyethyl)-2-oxazolidone.The present invention uses nonmetal nitrogenous organic molecule as catalyst system, and the use that effectively prevent due to metal catalyst causes metal ion to the pollution of Chan Wu oxazolidone, and cheap and easy to get; Catalyzer used in the present invention is stable non-metallic organic molecule, can be recovered utilization, and this catalyst system is environmentally friendly.
Description
Technical field
The invention belongs to fine chemical product and catalyze and synthesize field, relate to the method that one prepares 3-(2-hydroxyethyl)-2-oxazolidone.
Background technology
Oxazolidone is the very important five member ring heterocyclic compound of a class, is chiral auxiliary(reagent) and the reaction intermediate of organic synthesis and Polymer Synthesizing.Outside this, oxazolidone is Chang Zuowei bioactive agents also, is widely used in medicine and agriculture field.
Such as: Linezolid, first Shi oxazolidone antibacterial agent clinically.The importance of Ji Yu oxazolidone, Kai Fa oxazolidone efficient, new green synthesizing process is very meaningful.
Comparatively the industrial preparative method of Cheng Shu oxazolidone mainly contains following three kinds at present: the carbonylation reaction of alkamine compound and phosgene or carbon monoxide, the direct synthesis of propargylamine and carbonic acid gas, and the direct linked reaction of ethylenimine and carbonic acid gas.The phosgene that wherein first method uses has severe toxicity, and by-product hydrochloric acid meeting etching apparatus, atom utilization is low, unfriendly to environment; Carbon monoxide poisoning comparatively large, and inflammable and explosive, abnormally dangerous.By contrast, the Atom economy of the third method is the highest, more has research potential.In addition, carbonic acid gas has cheap and easy to get, renewable, nontoxic, abundance, the advantages such as environmental protection, is often regarded C1 synthon for the synthesis of in reaction.So ethylenimine and the even oxazolidone that is unified into of carbonic acid gas are ideal and effectively green synthetic methods.
Relative to carbonic acid gas and epoxy compounds addition synthesizing annular carbonate reaction simple, almost without the feature of side reaction, the method for carbonic acid gas and ethylenimine is limited to the dimerization of ethylenimine or the side reaction of poly.In catalyst system, ethylenimine Chengs also the be far from achievement in research of epoxy compounds synthesizing annular carbonate of oxazolidone with carbonic acid gas He many.
In sum, to Cheng oxazolidone with the anti-He of answering of ethylenimine be the research topic with important scientific meaning and application background with setting up stable, cheap organic molecule catalysis carbonic acid gas in research.
Summary of the invention
The object of this invention is to provide the method that one prepares 3-(2-hydroxyethyl)-2-oxazolidone.
The method preparing 3-(2-hydroxyethyl)-2-oxazolidone provided by the invention, comprise the steps: under the condition of nitrogenous compound as catalyzer, the 1-of compound shown in formula II (2-hydroxyethyl) ethyleneimine is carried out cyclization in carbon dioxide atmosphere, reacts complete and obtain compound 3-shown in described formula I (2-hydroxyethyl)-2-oxazolidone;
Under the condition of nitrogenous compound as catalyzer, the 1-of compound shown in formula II (2-hydroxyethyl) ethyleneimine is carried out cyclization in carbon dioxide atmosphere, reacts complete and obtain compound 3-shown in described formula I (2-hydroxyethyl)-2-oxazolidone;
Described nitrogenous compound is any one in compound shown in formula III-1 to formula III-19:
In aforesaid method, the consumption of described catalyzer to feed intake the 9-11% of mole dosage for compound 1-shown in described formula II (2-hydroxyethyl) ethyleneimine, is specially 10%.
In described cyclization step, temperature is 90-130 DEG C, is specially 110-130 DEG C;
Time is 10-20 hour, is specially 15-20 hour;
The pressure of carbon dioxide atmosphere is 25-35atm, is specially 30atm.
Described cyclization carries out in organic solvent.Concrete, described organic solvent is selected from least one in methyl alcohol, ethanol, n-propyl alcohol, ethylene glycol, butyl alcohol-tert, acetonitrile, toluene, Isosorbide-5-Nitrae-dioxane and DMF.
The amount ratio of compound 1-shown in described organic solvent and formula II (2-hydroxyethyl) ethyleneimine is 6ml:2mmol.
Reaction unit is the reaction unit of sealing, is specially stainless steel cauldron.
The present invention and traditional catalyst and technics comparing have the following advantages:
1. catalyst system is simple;
2. use cheap itrogenous organic substance as catalyzer, effectively save production cost;
3. catalyst activity is high, stable in properties, is easy to Separation and Recovery;
4. product and catalyzer can use simple fractionation by distillation, and catalyzer can recycle.
Accompanying drawing explanation
Fig. 1 is the nucleus magnetic hydrogen spectrum figure of embodiment 1 products therefrom.
Fig. 2 is the nuclear-magnetism carbon spectrogram of embodiment 1 products therefrom.
Embodiment
Below in conjunction with specific embodiment, the present invention is further elaborated, but the present invention is not limited to following examples.Described method is ordinary method if no special instructions.Described starting material all can obtain from open commercial sources if no special instructions.
Embodiment 1
Measure catalyzer 2 shown in formula III-1 respectively, 2 '; 2 "-terpyridyl 0.046g (0.2mmol), the 1-of compound shown in formula II (2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL organic solvent ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas that pressure is 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 58%.
As shown in Figure 1, as shown in Figure 2, as seen from the figure, this product structure is correct, is 3-shown in formula I (2-hydroxyethyl)-2-oxazolidone for carbon spectrum for the nucleus magnetic hydrogen spectrum of this embodiment products therefrom.
Embodiment 2
Measuring 2 respectively, 2 ', 2 "-terpyridyl 0.046g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL methyl alcohol joins in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 110 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 70%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 3
Measuring 2 respectively, 2 ', 2 "-terpyridyl 0.046g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL methyl alcohol joins in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 130 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 60%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 4
Measuring 2 respectively, 2 ', 2 "-terpyridyl 0.046g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL methyl alcohol joins in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 65%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 5
Measuring 2 respectively, 2 ', 2 "-terpyridyl 0.046g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL n-propyl alcohol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 53%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 6
Measuring 2 respectively, 2 ', 2 "-terpyridyl 0.046g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethylene glycol joins in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 50%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 7
Measure 2-picoline 0.019g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 55%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 8
Measure PA 0.019g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 50%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 9
Measure 2-amido-4,6-dimethyl pyrimidine 0.025g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 50%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 10
Measure triethylamine 0.020g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C, cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 28%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 11
Measure tri-n-butyl amine 0.037g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C, cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 30%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 12
Measure Tetramethyl Ethylene Diamine (TEMED) 0.023g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C, cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 53%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 13
Measure 1 respectively, 8-diazacyclo hendecene (DBU) 0.030g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 48%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 14
Measure 1 respectively, 4-diazabicylo [2.2.2] octane (DABCO) 0.022g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 50%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 15
Measure aniline 0.019g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 21%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 16
Measure methylphenylamine 0.021g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 10h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 30%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 17
Measure DMA 0.024g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 38%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 18
Measure positive tridecanoyl amine 0.045g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C, cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 5%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 19
Measure benzamide 0.024g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 5%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 20
Measure N respectively, N-dimethyl benzamide 0.030g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 20%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 21
Measure 2,3,4,5,6-penta fluoro benzene methane amide 0.042g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 5%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 22
Measure pyridine 0.016g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 36%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 23
Measure cyanophenyl 0.021g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 5%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 24
Measure acetonitrile 0.008g (0.2mmol) respectively, 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 15%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 25
Measuring 2 respectively, 2 ', 2 "-terpyridyl 0.046g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL1,2-ethylene dichloride join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 35%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 26
Measuring 2 respectively, 2 ', 2 "-terpyridyl 0.046g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL butyl alcohol-tert join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 20%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 27
Measuring 2 respectively, 2 ', 2 "-terpyridyl 0.046g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL acetonitrile join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 5%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 28
Measuring 2 respectively, 2 ', 2 "-terpyridyl 0.046g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL toluene joins in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 5%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 29
Measuring 2 respectively, 2 ', 2 "-terpyridyl 0.046g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL1,4-dioxane join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 5%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 30
Measure 2 respectively, 2 ', 2 "-terpyridyl 0.046g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mLN, dinethylformamide joins in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 5%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 31
Measuring 2 respectively, 2 ', 2 "-terpyridyl 0.023g (0.1mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL methyl alcohol joins in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 38%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Embodiment 32
Measuring 2 respectively, 2 ', 2 "-terpyridyl 0.046g (0.2mmol), 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL methyl alcohol joins in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 110 DEG C.Cyclization 15h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 47%.
The nuclear-magnetism result of this embodiment products therefrom is as identical in embodiment 1, repeats no more herein.
Comparative example 1
Under catalyst-free condition, add 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) and 6mL ethanol joins in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is 15%.
Comparative example 2
Measure terpyridyl 0.046g (0.2mmol) and 1-(2-hydroxyethyl) ethyleneimine 0.174g (2mmol) respectively, join in the stainless steel autoclave of 25-mL.After being sealed by reactor, 25 DEG C time, be filled with the carbonic acid gas of 30atm.Stir, be heated to 90 DEG C.Cyclization 20h is carried out in insulation.Then room temperature is cooled to, venting.The productive rate of reaction result: 3-(2-hydroxyethyl)-2-oxazolidone is <5%.
Claims (10)
1. a method for the 3-of compound shown in preparation formula I (2-hydroxyethyl)-2-oxazolidone, comprises the steps:
Under the condition of nitrogenous compound as catalyzer, the 1-of compound shown in formula II (2-hydroxyethyl) ethyleneimine is carried out cyclization in carbon dioxide atmosphere, reacts complete and obtain compound 3-shown in described formula I (2-hydroxyethyl)-2-oxazolidone;
Described nitrogenous compound is any one in compound shown in formula III-1 to formula III-19:
CH
3CN
Formula III-19.
2. method according to claim 1, is characterized in that: the consumption of described catalyzer to feed intake the 9-11% of mole dosage for compound 1-shown in described formula II (2-hydroxyethyl) ethyleneimine.
3. method according to claim 2, is characterized in that: the consumption of described catalyzer to feed intake 10% of mole dosage for compound 1-shown in described formula II (2-hydroxyethyl) ethyleneimine.
4. method according to claim 1, is characterized in that: in described cyclization step, and temperature is 90-130 DEG C;
Time is 10-20 hour;
The pressure of carbon dioxide atmosphere is 25-35atm.
5. method according to claim 4, is characterized in that: in described cyclization step, and temperature is 110-130 DEG C;
Time is 15-20 hour;
The pressure of carbon dioxide atmosphere is 30atm.
6. method according to claim 1, is characterized in that: described cyclization carries out in organic solvent.
7. method according to claim 6, is characterized in that: described organic solvent is selected from least one in methyl alcohol, ethanol, n-propyl alcohol, ethylene glycol, butyl alcohol-tert, acetonitrile, toluene, Isosorbide-5-Nitrae-dioxane and DMF.
8. method according to claim 6, is characterized in that: the amount ratio of compound 1-shown in described organic solvent and formula II (2-hydroxyethyl) ethyleneimine is 6ml:2mmol.
9., according to the arbitrary described method of claim 1-8, it is characterized in that: described cyclization carries out in the reaction unit of sealing.
10. method according to claim 9, is characterized in that: described reaction unit is stainless steel cauldron.
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| Amine functionalized MCM-41 as a green,efficient, and heterogeneous catalyst for the regioselective synthesis of 5-aryl-2-oxazolidinones, from CO2 and aziridines;Nale, Deepak B. et al.;《Applied Catalysis, A: General》;20131017;第469卷;340-349 * |
| Cycloaddition of tertiary aziridines and carbon dioxide using a recyclable organocatalyst, 1,3-di-tert-butylimidazolium-2-carboxylate:straightforward access to 3-substituted 2-oxazolidones;Ueno, Atsushi et al.;《Green Chemistry》;20121025;第15卷(第2期);425-430 * |
| 温和条件下催化吖丙啶与二氧化碳环加成反应合成恶唑烷酮;张志超 等.;《染料与染色》;20060831;第43卷(第4期);32-34 * |
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