CN107253923A - A kind of synthetic method and purposes of acetylurea dimer crystalline compounds - Google Patents
A kind of synthetic method and purposes of acetylurea dimer crystalline compounds Download PDFInfo
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- CN107253923A CN107253923A CN201710668183.8A CN201710668183A CN107253923A CN 107253923 A CN107253923 A CN 107253923A CN 201710668183 A CN201710668183 A CN 201710668183A CN 107253923 A CN107253923 A CN 107253923A
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- acetylurea
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 18
- GKRZNOGGALENQJ-UHFFFAOYSA-N n-carbamoylacetamide Chemical class CC(=O)NC(N)=O GKRZNOGGALENQJ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000010189 synthetic method Methods 0.000 title claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000013078 crystal Substances 0.000 claims abstract description 11
- -1 acetylurea dimer compound Chemical class 0.000 claims abstract description 10
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- QROGIFZRVHSFLM-QHHAFSJGSA-N [(e)-prop-1-enyl]benzene Chemical compound C\C=C\C1=CC=CC=C1 QROGIFZRVHSFLM-QHHAFSJGSA-N 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 4
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000002825 nitriles Chemical class 0.000 claims abstract description 3
- 229940117360 ethyl pyruvate Drugs 0.000 claims abstract 2
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910002804 graphite Inorganic materials 0.000 claims 1
- 239000010439 graphite Substances 0.000 claims 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract description 10
- 235000005074 zinc chloride Nutrition 0.000 abstract description 5
- 239000011592 zinc chloride Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- CXUIJJGHMZWHAG-UHFFFAOYSA-N CC(=O)NC(N)=O.CC(=O)NC(N)=O Chemical compound CC(=O)NC(N)=O.CC(=O)NC(N)=O CXUIJJGHMZWHAG-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000010192 crystallographic characterization Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical class C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0245—Nitrogen containing compounds being derivatives of carboxylic or carbonic acids
- B01J31/0249—Ureas (R2N-C(=O)-NR2)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
- B01J2231/342—Aldol type reactions, i.e. nucleophilic addition of C-H acidic compounds, their R3Si- or metal complex analogues, to aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A kind of acetylurea dimer compound, its chemical formula is as follows:
Description
First, technical field
The present invention relates to a kind of compound and preparation method thereof, more particularly to a kind of nitrogen-containing compound and preparation method thereof, definitely
It is a kind of synthetic method of acetylurea dimer crystalline compounds that ground, which is said,.
2nd, background technology
Acetyl carbamide compound is important medicine intermediate, its synthetic method and the existing document report of application【1-3】
Bibliography:
1. Acetylcarbamide complexes of some lanthanide bromides and chlorides:
Syntheses and structures
Alikberova, L. Yu.; Al'bov, D. V.; Bushmeleva, A. S.; Fedorova, G. A.;
Kravchenko, V. V., Russian Journal of Coordination Chemistry (2014), 40 (12),
918-924.
2. New method of preparing N- acetylurea, Kurbanova, M. M. Izvestiya
Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya (2004), 47
(8), 165.
3. Crystallographic characterization of monoacylated ureas, Hartung,
Helmut; Lux, Georg; Hennicke, Rainer;Schellenberger, Alfred, Zeitschrift fuer
Chemie (1973), 13 (6), 234-235.
3rd, the content of the invention
It is contemplated that the compound ligand needed for medicine provides a kind of effective catalyst is particularly prepared for organic synthesis field,
Technical problem to be solved is to select corresponding raw material and set up corresponding method synthetic catalyst part.
(One)Compound alleged by the present invention is the compound shown in below formula (I):
Its chemical name:Acetylurea dimer.
The compound(Ⅰ)Synthetic method be that a cyano group propenyl benzene and acetylurea are molten in catalyst zinc chloride and absolute methanol
Reacted in liquid,
The chemical equation is as follows:
This acetylurea dimer compound (I) synthetic method includes synthesis, separation and purified, and described synthesis is anhydrous and oxygen-free bar
Under part, 0.6420g is weighed(0.005mol)Zinc chloride, acetylurea 1.0046g and a cyano group propenyl benzene 1.3275g are put into
In two mouthfuls of flasks of 100mL, adding 20mL absolute methanols and being stirred at room temperature dissolves it;After reaction 48 hours, heat filtering adds dichloro
Methane and absolute ethyl alcohol, and solution is volatilized naturally, obtain white crystal.
The reaction mechanism of the reaction can be presumed as follows:
Intermolecular polymerization shape occurs for acetylurea acetylurea in the presence of absolute methanol, a cyano group propenyl benzene and catalyst zinc chloride
Into target compound I.
The preparation of this acetylurea dimer compound (I), using simple, efficient methodology of organic synthesis, one-step synthesis, warp
X- diffraction, NMR, IR and elementary analysis determine its structure, its as catalyst benzaldehyde nitrile silicification reaction and pyruvic acid second
Certain catalytic effect is shown in the Henle reaction of ester, its conversion ratio is respectively up to 18% and 86%.
4th, illustrate
Fig. 1 is the single crystal diffraction figure of acetylurea dimer compound (I).
5th, embodiment
The preparation of acetylurea dimer compound (I)
Weigh 0.6420g(0.005mol)Zinc chloride, acetylurea 1.0046g and a cyano group propenyl benzene 1.3275g are put into 100mL circles
In the flask of bottom, add 30mL absolute methanols and stopping reaction heat filtering after 48h be stirred at room temperature, add dichloromethane and absolute ethyl alcohol,
And solution volatilizees naturally, obtain white crystal;Yield is 58%, 215-217 °C of fusing point;Elemental analysis data C6H12N4O4, C:
35.29%; H:5.92%;N:27.44%;Measured value:C 35.53%; H:5.71%;N:27.72%;HRMS (e/m) theoretical value:
204.0859;Measured value:204.0843;1HNMR (600MHz, CDCl3, 27℃), δ (ppm) = 10.12(s,
2H), 7.89-7.91(m, 2H), 6.81(s, 2H), 2.0(s, 6H); 13C NMR (150 MHz, CDCl3) 170.8
(x2), 153.2(x2), 22.4(x2);Ir data (KBr, cm-1):3379,3333,3230,1691,
1671,1417,1370,1256,1099,1034,943,875,813,699,570,451;
Nitrogen compound crystal data is as follows:
Empirical formula C6H12N4O4
Molecular weight 204.20
Temperature 100.01 (10) K
Wavelength 0.71073
Crystallographic system, Space group Monoclinic system, P21
Cell parameter a=6.6827 (3) α=90 °
b = 5.0880(2) Å β = 96.655(4)°.
c = 6.9153(3) Å γ = 90 °
Volume 233.545(18)Å^3
Charge density 2,1.452Mg/m^3
The mm^-1 of absorption correction parameter 1.051
Number of electrons 108.0 in unit cell
The x 0.1x 0.1mm of crystal size 0.1
The to 145.472 of scope 12.888 at Theta angles
HKL index capture range -6<=h<=8, -6<k<=4, -8<l<=8
Collection/independent diffraction data 758/ 628 [R (int)=0.0110]
The method Multi Slice Mode of absorption correction
The Matrix least square method for the method F^2 that refine is used
Number/number of parameters 1326/0/111 of data number/use limitation
The method 1.045 that refine is used
The uniformity factor R 1=0.0256 of point diffraction, ω R2=0.0647
The identical factor R 1=0.0261 of observable diffraction, ω R2=0.0648
Maximum summit and the and -0.19 e. ^-3 of peak valley 0.12 on difference Fourier figure
The typical bond distance's data of crystal:
N(1)-C(3) 1.314(14)
N(1)-H(1A) 0.8600
N(1)-H(1B) 0.8600
N(2)-C(1) 1.346(18)
N(2)-C(3) 1.398(11)
N(2)-H(2) 0.8600
N(3)-C(6) 1.213(16)
N(3)-H(3A) 0.8600
N(3)-H(3B) 0.8600
N(4)-C(4) 1.307(19)
N(4)-C(6) 1.552(16)
N(4)-H(4) 0.8600
O(1)-C(1) 1.169(17)
O(2)-C(3) 1.209(13)
O(3)-C(6) 1.225(14)
O(4)-C(4) 1.34(2)
C(1)-C(2) 1.505(17)
C(2)-H(2A) 0.9600
C(2)-H(2B) 0.9600
C(2)-H(2C) 0.9600
C(4)-C(5) 1.429(16)
C(5)-H(5A) 0.9600
C(5)-H(5B) 0.9600
C(5)-H(5C) 0.9600
The typical bond angle data of crystal:
C(3)-N(1)-H(1A) 120.0
C(3)-N(1)-H(1B) 120.0
H(1A)-N(1)-H(1B) 120.0
C(1)-N(2)-C(3) 134.7(14)
C(1)-N(2)-H(2) 112.6
C(3)-N(2)-H(2) 112.7
C(6)-N(3)-H(3A) 120.0
C(6)-N(3)-H(3B) 120.0
H(3A)-N(3)-H(3B) 120.0
C(4)-N(4)-C(6) 125.0(14)
C(4)-N(4)-H(4) 117.5
C(6)-N(4)-H(4) 117.5
O(1)-C(1)-N(2) 119.1(12)
O(1)-C(1)-C(2) 129.0(13)
N(2)-C(1)-C(2) 111.8(11)
C(1)-C(2)-H(2A) 109.5
C(1)-C(2)-H(2B) 109.4
H(2A)-C(2)-H(2B) 109.5
C(1)-C(2)-H(2C) 109.5
H(2A)-C(2)-H(2C) 109.5
H(2B)-C(2)-H(2C) 109.5
O(2)-C(3)-N(1) 123.2(7)
O(2)-C(3)-N(2) 120.2(11)
N(1)-C(3)-N(2) 116.6(11)
N(4)-C(4)-O(4) 123.3(11)
N(4)-C(4)-C(5) 121.2(15)
O(4)-C(4)-C(5) 115.5(13)
C(4)-C(5)-H(5A) 109.5
C(4)-C(5)-H(5B) 109.5
H(5A)-C(5)-H(5B) 109.5
C(4)-C(5)-H(5C) 109.4
H(5A)-C(5)-H(5C) 109.5
H(5B)-C(5)-H(5C) 109.5
N(3)-C(6)-O(3) 137.1(13)
N(3)-C(6)-N(4) 114.9(11)
O(3)-C(6)-N(4) 108.0(11)
2. nitrile silicification reaction application
2- phenyl -2-(Three silyloxies)Propionitrile
The ml (3.3mmol) of 0.2mmol compound I, benzaldehyde 0.1mL, TMSCN 0.3,2mL absolute methanols, in succession
Added under 30 ~ 35 C, after 48 hours, add water quenching and go out after post layer(Petroleum ether/dichloromethane:5/1), obtain colorless oil
Liquid, conversion ratio:18.0 %;1H NMR (300MHz, CDCl3) 7.56–7.59 (m, 0.9 Hz, 2H), 7.31–
7.34 (m, 3H), 5.43 (s, 1H), 0.16 (s, 9H). 13C NMR (75 MHz, CDCl3) 136.1, 128.8
(x2), 126.2(x2), 119.1, 63.5, -0.39(x3)。
3. Henle reaction application
0.0675g compounds(I), be placed in 25mL flasks, sequentially add 1mL tetrahydrofurans, 0.3 mL nitromethanes and
0.5mmol ethyl pyruvates, stirring at normal temperature reaction 48h, separately sampled progress1HNMR detects that its conversion ratio is 86%;1 H NMR
(CDCl 3 ): δ ) 4.86 (d,J =13.8 Hz, 1H), 4.58 (d, J =13.8 Hz, 1H), 4.34 (m,
2H), 3.85(s, 1H), 1.46 (s, 3H), 1.33 (t, J ) 7.2 Hz, 3H).13 C NMR (CDCl 3 ):δ=
173.4, 80.9, 72.4, 63.0, 23.8, 13.9。
Claims (4)
1. a kind of acetylurea dimer compound, it is characterized in that as the compound shown in below formula:
(Ⅰ).
2. as the acetylurea dimer crystalline compounds described in claim 1(I), 273(2)At a temperature of k, in Oxford, X- is penetrated
On line single crystal diffractometer, with the monoclinic system through graphite monochromator monochromatization, P21,Cell parameter:a = 6.6827(3) Å α =
90°;b = 5.0880(2) Å β = 96.655(4)°.;c = 6.9153(3) Å γ = 90 °.
3. the acetylurea dimer crystalline compounds described in claim 1(I), 273(2)At a temperature of k, in Oxford X-ray
On single crystal diffractometer, with through acetylurea dimer crystalline compounds(I)Synthetic method, including synthesis, separation and purify, it is described
Synthesis be anhydrous and oxygen-free under the conditions of, weigh an acetylurea 1.0046g and cyano group propenyl benzene 1.3275g and be put into two mouthfuls of burnings of 100mL
In bottle, adding 20mL absolute methanols and being stirred at room temperature dissolves it;After reaction 48 hours, heat filtering adds dichloromethane and anhydrous
Ethanol, and solution is volatilized naturally, obtain white crystal.
4. the purposes of the acetylurea dimer crystalline compounds (I) described in claim 1, is the nitrile as catalyst in benzaldehyde
Applied in the Henle reaction of silication and ethyl pyruvate, its conversion ratio is respectively up to 18% and 86%.
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Cited By (4)
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CN107602414A (en) * | 2017-10-29 | 2018-01-19 | 合肥祥晨化工有限公司 | A kind of synthetic method and purposes of diphenyl-ketoxime dimer crystalline compounds |
CN107652205A (en) * | 2017-10-24 | 2018-02-02 | 合肥祥晨化工有限公司 | A kind of synthetic method and purposes of imines crystalline compounds |
CN107698465A (en) * | 2017-11-14 | 2018-02-16 | 合肥祥晨化工有限公司 | A kind of synthetic method of acetylurea crystalline compounds |
CN112480126A (en) * | 2020-12-11 | 2021-03-12 | 合肥工业大学 | Preparation and application of 5-alkyl quinazoline derivative |
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2017
- 2017-08-07 CN CN201710668183.8A patent/CN107253923A/en not_active Withdrawn
- 2017-10-19 CN CN201710975450.6A patent/CN107674004A/en active Pending
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CN107652205A (en) * | 2017-10-24 | 2018-02-02 | 合肥祥晨化工有限公司 | A kind of synthetic method and purposes of imines crystalline compounds |
CN107602414A (en) * | 2017-10-29 | 2018-01-19 | 合肥祥晨化工有限公司 | A kind of synthetic method and purposes of diphenyl-ketoxime dimer crystalline compounds |
CN107698465A (en) * | 2017-11-14 | 2018-02-16 | 合肥祥晨化工有限公司 | A kind of synthetic method of acetylurea crystalline compounds |
CN107698465B (en) * | 2017-11-14 | 2019-07-05 | 合肥祥晨化工有限公司 | A kind of synthetic method of acetylurea crystalline compounds |
CN112480126A (en) * | 2020-12-11 | 2021-03-12 | 合肥工业大学 | Preparation and application of 5-alkyl quinazoline derivative |
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