CN109748829B - Preparation method of oxalyl sulfonyl hydrazide and application of oxalyl sulfonyl hydrazide in olefin sulphonation reaction - Google Patents
Preparation method of oxalyl sulfonyl hydrazide and application of oxalyl sulfonyl hydrazide in olefin sulphonation reaction Download PDFInfo
- Publication number
- CN109748829B CN109748829B CN201811514887.0A CN201811514887A CN109748829B CN 109748829 B CN109748829 B CN 109748829B CN 201811514887 A CN201811514887 A CN 201811514887A CN 109748829 B CN109748829 B CN 109748829B
- Authority
- CN
- China
- Prior art keywords
- oxalyl
- sulfonyl hydrazide
- reaction
- olefin
- beta
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 29
- -1 oxalyl sulfonyl Chemical group 0.000 title claims abstract description 28
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 239000007800 oxidant agent Substances 0.000 claims abstract description 4
- 230000001590 oxidative effect Effects 0.000 claims abstract description 4
- 238000007259 addition reaction Methods 0.000 claims abstract description 3
- 230000003647 oxidation Effects 0.000 claims abstract description 3
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract description 12
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 7
- 239000003513 alkali Substances 0.000 abstract description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- BBNUGJZCLZHILC-UHFFFAOYSA-N 1-(3-bromophenyl)-2-(4-methylphenyl)sulfonylethanone Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC(=O)C1=CC=CC(Br)=C1 BBNUGJZCLZHILC-UHFFFAOYSA-N 0.000 description 1
- JGMRIHQYBXLTGM-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(4-methylphenyl)sulfonylethanone Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC(=O)C1=CC=C(Br)C=C1 JGMRIHQYBXLTGM-UHFFFAOYSA-N 0.000 description 1
- UFXWUSAAGJDPOF-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-2-phenylpropan-2-ol Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC(C)(O)C1=CC=CC=C1 UFXWUSAAGJDPOF-UHFFFAOYSA-N 0.000 description 1
- KQJQPCJDKBKSLV-UHFFFAOYSA-N 1-bromo-3-ethenylbenzene Chemical compound BrC1=CC=CC(C=C)=C1 KQJQPCJDKBKSLV-UHFFFAOYSA-N 0.000 description 1
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 description 1
- VSTXCZGEEVFJES-UHFFFAOYSA-N 1-cycloundecyl-1,5-diazacycloundec-5-ene Chemical compound C1CCCCCC(CCCC1)N1CCCCCC=NCCC1 VSTXCZGEEVFJES-UHFFFAOYSA-N 0.000 description 1
- RFQXSRPFYWMUDV-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonyl-1-phenylethanone Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC(=O)C1=CC=CC=C1 RFQXSRPFYWMUDV-UHFFFAOYSA-N 0.000 description 1
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000005362 aryl sulfone group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811514887.0A CN109748829B (en) | 2018-12-12 | 2018-12-12 | Preparation method of oxalyl sulfonyl hydrazide and application of oxalyl sulfonyl hydrazide in olefin sulphonation reaction |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811514887.0A CN109748829B (en) | 2018-12-12 | 2018-12-12 | Preparation method of oxalyl sulfonyl hydrazide and application of oxalyl sulfonyl hydrazide in olefin sulphonation reaction |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109748829A CN109748829A (en) | 2019-05-14 |
CN109748829B true CN109748829B (en) | 2021-08-17 |
Family
ID=66403620
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201811514887.0A Active CN109748829B (en) | 2018-12-12 | 2018-12-12 | Preparation method of oxalyl sulfonyl hydrazide and application of oxalyl sulfonyl hydrazide in olefin sulphonation reaction |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109748829B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111807986B (en) * | 2020-06-22 | 2023-04-11 | 江苏大学 | Synthetic method of oxalyl hydrazine ligand and application of oxalyl hydrazine ligand in C-N bond coupling reaction |
CN111978216B (en) * | 2020-09-22 | 2023-02-03 | 西南医科大学 | Preparation method of beta-carbonyl sulfone compound |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR102013012646B1 (en) * | 2013-05-22 | 2020-12-08 | Universidade Federal Do Rio De Janeiro | sulfonylhydrazonic compound, process for obtaining the sulfonylhydrazonic compound and pharmaceutical compositions |
CN106432004B (en) * | 2016-09-28 | 2018-08-28 | 济南大学 | A kind of synthetic method of 3- sulfuryls alcohol compound |
CN108440349B (en) * | 2018-05-11 | 2020-10-20 | 上海李氏化学科技有限公司 | Preparation method of chiral optical pure p-toluenesulfinamide |
-
2018
- 2018-12-12 CN CN201811514887.0A patent/CN109748829B/en active Active
Also Published As
Publication number | Publication date |
---|---|
CN109748829A (en) | 2019-05-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN112592376B (en) | Method for preparing mannose-containing derivative for post-polymerization modification by using double-click chemistry combination | |
CN109748829B (en) | Preparation method of oxalyl sulfonyl hydrazide and application of oxalyl sulfonyl hydrazide in olefin sulphonation reaction | |
CN110627693B (en) | Allyl sulfone compound and preparation method and application thereof | |
CN107033212B (en) | A kind of ursolic acid derivative and its preparation method and application with anti-inflammatory activity | |
Bukownik et al. | Synthetic receptors. 3, 6-Anhydro-7-benzenesulfonamido-1, 7-dideoxy-4, 5-O-isopropylidene-D-altro-hept-1-ynitol: A useful component for the preparation of chiral water-soluble cyclophanes based on carbohydrate precursors | |
CN113698325A (en) | Method for preparing alkyl sulfonyl fluoride | |
JP5646706B2 (en) | Method for producing C-glycoside derivative | |
CN109232331B (en) | Process for preparing β -ketosulfone or β -hydroxysulfone by reaction of substituted olefin with sulfonyl hydrazide derivative | |
CN114634482A (en) | Diazo difluoromethylation reagent and synthesis method and application thereof | |
CN112321553B (en) | Method for synthesizing 3-position difluoromethyl substituted coumarin derivative from aryl alkyne acid ester | |
CN110511193A (en) | A kind of α -one thioamide analog compound and its synthetic method | |
CN111269074A (en) | Preparation method of α -halogenated trifluoromethyl substituted alkane | |
CN104974121A (en) | Synthesis method of 3-aryl-formyl coumarin derivatives | |
CN115010753A (en) | Method for preparing phosphorylated gem-difluorodiene compound in aqueous phase | |
CN111253331B (en) | Method for synthesizing spiroisoxazoline by using dihydrochalcone as raw material | |
CN113620848A (en) | Reaction method of thiophenol and o-diiodobenzene | |
CN106674198A (en) | Preparation method for key intermediate rabeprazole thioether | |
CN110386889B (en) | Synthesis method of NSC128981 | |
CN108727323B (en) | Method for catalytically synthesizing trifluoromethyl substituted homoisoflavone compound by using N-heterocyclic carbene | |
CN107629039B (en) | The preparation method and intermediate of deuterated acrylamide | |
CN111635401A (en) | Copper complex promoted 7-fluoroimidazo [1,2-a ] pyridine synthesis method | |
CN109320554B (en) | Novel method for synthesizing practical acetaminoacrylate compound | |
CN103382208B (en) | The preparation method of Arglabin | |
JP5305697B2 (en) | Method for producing α-D-mannopyranoside derivative | |
CN112300035A (en) | Preparation method of dithioacetal derivative |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
TA01 | Transfer of patent application right | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20210726 Address after: 201507 building 3, No. 88, pingye Road, Caojing Town, Jinshan District, Shanghai Applicant after: Shanghai Mahou New Material Technology Co.,Ltd. Address before: Zhenjiang City, Jiangsu Province, 212013 Jingkou District Road No. 301 Applicant before: JIANGSU University |
|
GR01 | Patent grant | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of oxalyl sulfonyl hydrazide and its application in olefin sulfonation reaction Granted publication date: 20210817 Pledgee: Agricultural Bank of China Limited Shanghai Fengxian Branch Pledgor: Shanghai Mahou New Material Technology Co.,Ltd. Registration number: Y2024310000073 |