Process for the preparation of 3-hydroxyacrylonitrile metal salts

A technology of hydroxyacrylonitrile and metal salts, applied in the direction of organic chemistry, etc., can solve the problems of high reaction operation pressure, complicated preparation method operation, and hidden safety hazards in operation, and achieve good yield, convenient preparation, and reduce unsafe factors Effect

Active Publication Date: 2005-03-16
杭州科本药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] The preparation method is complicated to operate, the reaction operation pressure is high, and there are potential safety hazards in the operation

Method used

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  • Process for the preparation of 3-hydroxyacrylonitrile metal salts
  • Process for the preparation of 3-hydroxyacrylonitrile metal salts
  • Process for the preparation of 3-hydroxyacrylonitrile metal salts

Examples

Experimental program
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Effect test

Embodiment 1

[0037] Add 90 kg of acetonitrile, 400 kg of toluene, and 150 kg of sodium methoxide into a 1000-liter stainless steel reactor, and add 280 kg of methyl formate at 25°C. After the addition, stir for 5 hours under 3 atmospheres, that is The sodium salt solution of 3-hydroxyacrylonitrile was obtained.

[0038] Then, at 30°C, the sodium salt solution of the obtained 3-hydroxyacrylonitrile was added to a 2000-liter reaction kettle equipped with 700 kg of salt alcohol ethanol, and after stirring for 2.5 hours, it was neutralized to neutral with alkali, evaporated Remove the solvent, add 400 kg of toluene, 150 kg of sodium methoxide, and 200 kg of urea to the residue, react at 70°C for 4 hours, cool, neutralize with glacial acetic acid, filter, and recrystallize the obtained solid with acetic acid to obtain cytosine 130 kg, melting point: >280°C, content: 99.0% (HPLC, area normalization method), 99.8% (reference method). Based on acetonitrile, the yield is: 53.2%.

Embodiment 2

[0040] Add 90 kilograms of acetonitrile, 400 kilograms of toluene, and 150 kilograms of sodium methoxide in a 1000-liter stainless steel reactor, and add 300 kilograms of ethyl formate at 20 ° C. After the addition, continue stirring for 5 hours under 3 atmospheres, that is, The sodium salt solution of 3-hydroxyacrylonitrile was obtained.

[0041] Then, at 30°C, the sodium salt solution of the obtained 3-hydroxyacrylonitrile was added to a 2000-liter reaction kettle equipped with 700 kg of salt alcohol ethanol, stirred for 2.5 hours, neutralized with alkali to neutrality, and evaporated. Solvent, add 400 kg of toluene, 150 kg of sodium methoxide, and 200 kg of urea to the residue, react at 70°C for 4 hours, cool, neutralize with glacial acetic acid, filter, and recrystallize the obtained solid with acetic acid to obtain cytosine 137 kg, melting point: >280°C, content: 99.1%% (HPLC, area normalization method), 101.2% (HPLC, reference substance method). Based on acetonitrile, t...

Embodiment 3

[0043] Add 90 grams of acetonitrile, 400 grams of benzene, and 290 grams of sodium isopropoxide into a 1000 mL autoclave, and add 300 grams of isopropyl formate at 25°C. After the addition is complete, continue stirring for 5 hours at 3 atmospheres , That is, the sodium salt solution of 3-hydroxyacrylonitrile.

[0044] Then, at 30°C, the resulting sodium salt solution of 3-hydroxyacrylonitrile was added to a 2000 mL three-necked flask containing 700 grams of salt alcohol ethanol, stirred for 2.5 hours, neutralized to neutral with alkali, evaporated to Solvent, add 400 grams of xylene, 150 grams of sodium methoxide, and 200 grams of urea to the residue, react at 70°C for 4 hours, cool, add glacial acetic acid to neutralize, filter, and recrystallize the obtained solid with acetic acid to obtain cell 133 grams of pyrimidine, melting point: >280°C, content: 99.0%% (HPLC, area normalization method), 99.9% (HPLC, reference substance method). Based on acetonitrile, the yield is: 54...

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Abstract

The invention discloses a process for the preparation of 3-hydroxyacrylonitrile metal salts which comprises the steps of, subjecting acetonitrile and formic acid ester to condensation reaction under the action of metal alkyl oxide at 20-60 deg. C and 1-5 barometric pressure. The process for the preparation of 3-hydroxyacrylonitrile metal salts provided by the invention can realize good yield and convenient operation in preparing cytosine.

Description

(1) Technical field [0001] The invention relates to a preparation method of 3-hydroxyacrylonitrile metal salt. (2) Background technology [0002] Cytosine is an important chemical raw material, which is indispensable for the industrial production of the main drug for AIDS and the anti-hepatitis B drug lamivudine, anticancer drugs gemcitabine, enoxitabine and 5-fluorocytosine basic ingredients. [0003] In the prior art, the synthesis of cytosine is mainly through three routes of 3-alkoxyacrylonitrile, 3,3-dialkoxypropionitrile and mixtures thereof: [0004] 1. Preparation of cytosine by ring closure of 3-alkoxyacrylonitrile and urea (Theis, C. et al, DE3206878 (1983), Ube Industries, Ltd., JP 59-93059 (1984); Loquai, H. et al , DE 3434142 (1986)): [0005] [0006] 2. Preparation of cytosine by cyclization of 3,3-dialkoxypropionitrile and urea (Ube Industries, Ltd., JP 59-93060 (1984); Itter.F.A., DE 3906855 (1990)): [0007] [0008] 3. Preparation of cytosine by ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/15C07C255/30
Inventor 游金宗蒋善会
Owner 杭州科本药业有限公司
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