CN107674004A - 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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- CN107674004A CN107674004A CN201710975450.6A CN201710975450A CN107674004A CN 107674004 A CN107674004 A CN 107674004A CN 201710975450 A CN201710975450 A CN 201710975450A CN 107674004 A CN107674004 A CN 107674004A
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- acetylurea
- dimer
- crystalline compounds
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 17
- GKRZNOGGALENQJ-UHFFFAOYSA-N n-carbamoylacetamide Chemical class CC(=O)NC(N)=O GKRZNOGGALENQJ-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 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 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 11
- -1 acetylurea dimer compound Chemical class 0.000 claims abstract description 10
- 239000013078 crystal Substances 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 7
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 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
- 125000003963 dichloro group Chemical group Cl* 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
- 238000000926 separation method Methods 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
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/50—Y being a hydrogen or an acyclic carbon atom
-
- 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
- C07C273/1863—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 from urea
-
- 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 are 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 medicine is particularly prepared for organic synthesis field provides a kind of compound ligand needed for effective catalyst,
Technical problem to be solved is to select corresponding raw material and establish corresponding method synthetic catalyst part.
(1) 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 purifying, 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 makes its dissolving；After reaction 48 hours, heat filtering, dichloro is added
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 after 48h is stirred at room temperature in 30mL absolute methanols and stop reaction heat filtering, 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,
1H), 7.89-7.91(m, 1H), 6.81(s, 1H), 2.0(s, 3H); 13C NMR (150 MHz, CDCl3)
170.8, 153.2, 22.4；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 293 (2) K
Wavelength 0.71073
Crystallographic system, Space group Monoclinic system, P21
Cell parameter a=7.012 (3) α=90 °
b = 5.088(3) Å β = 98.208(10)°.
c = 13.674(7) Å γ = 90 °
Volume 482.9（4）Å^3
Charge density 2,1.404Mg/m^3
The mm^-1 of absorption correction parameter 0.118
Number of electrons 216 in unit cell
The 70x 0.140x 0.100mm of crystal size 0.1
The to 24.999 of scope 1.505 at Theta angles
HKL index capture range -8<=h<=6, -6<k<=6, -15<l<=16
Collection/independent diffraction data 2592/ 1619 [R (int)=0.0203]
The method Multi Slice Mode of absorption correction
The Matrix least square method for the method F^2 that refine uses
Number/number of parameters 1619/7/129 of data number/use limitation
The method 1.901 that refine uses
The uniformity factor R 1=0.1269 of point diffraction, ω R2=0.4180
The identical factor R 1=0.1438 of observable diffraction, ω R2=0.4487
And -0.866 e. the ^-3 of maximum summit and peak valley 0.744 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 is detected, and 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)
- A kind of 1. 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 = 7.012(3) Å α = 90°；b = 5.088(3) Å β = 98.208(10)°.；c = 13.674(7) Å γ = 90 °.
- 3. the acetylurea dimer crystalline compounds（I）Synthetic method, including synthesize, separate and purify, described synthesis is Under the conditions of anhydrous and oxygen-free, weigh acetylurea 1.0046g and a cyano group propenyl benzene 1.3275g is put into two mouthfuls of flasks of 100mL, add 20mL absolute methanols, which are stirred at room temperature, makes its dissolving；After reaction 48 hours, heat filtering, dichloromethane and absolute ethyl alcohol are added, and will Solution volatilizees naturally, obtains 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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| 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 |
| 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 |
| CN112480126B (en) * | 2020-12-11 | 2022-03-11 | 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
Non-Patent Citations (2)
| Title |
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| M. G. VORONKOV等: "Acyl Iodides in Organic Synthesis.Reactions of Acetyl Iodide with Urea, Thiourea,and Their N,N′-Disubstituted Derivatives", 《RUSSIAN JOURNAL OF ORGANIC CHEMISTRY》 * |
| 曾柏清: "催化醛的不对称硅腈化反应研究", 《中国优秀硕士学位论文全文数据库》 * |
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| CN107253923A (en) | 2017-10-17 |
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