Method for preparing 4,6-dihydroxy-pyrimidine from byproduct hydrocyanic acid of acrylonitrile

A technology of dihydroxypyrimidine and hydrocyanic acid, applied in 4 fields, to achieve the effect of less generation of three wastes, less environmental pollution, and low unit consumption of raw materials

Active Publication Date: 2014-01-08
YINGKOU YINGXIN CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] There is no literature report on the synthesis of 4,6-dihydroxypyrimidine using formamidine acetate

Method used

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  • Method for preparing 4,6-dihydroxy-pyrimidine from byproduct hydrocyanic acid of acrylonitrile
  • Method for preparing 4,6-dihydroxy-pyrimidine from byproduct hydrocyanic acid of acrylonitrile
  • Method for preparing 4,6-dihydroxy-pyrimidine from byproduct hydrocyanic acid of acrylonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In a 500ml reaction bottle, add 200ml of solvent toluene and 37g of methanol, stir and cool down to below -20°C, add 27g of hydrocyanic acid, start to pass in 42g of dry hydrogen chloride gas, control the temperature not to exceed 0°C for 8 hours, filter to obtain Aminomethyl ether hydrochloride.

[0021] For the iminomethyl methyl ether hydrochloride obtained in the previous step, add 93g of ammonium acetate and dissolve it in 200ml of anhydrous methanol in portions below -5°C, stir vigorously for 1 hour, heat up to room temperature and react for 2 hours, and heat up to The reaction was continued at 40°C for 1 hour, and white precipitated ammonium chloride gradually precipitated, cooled down, and filtered.

[0022] The filtrate is heated to reflux, and at the same time, dry ammonia gas is introduced at a certain speed for 2 to 2.5 hours, and about 85g of ammonia gas is introduced, and a white solid is gradually precipitated in the reaction bottle. After cooling down, f...

Embodiment 2

[0025] In a 500ml reaction bottle, add 200ml of solvent toluene and 46g of ethanol, stir and cool down to below -15°C, add 27g of hydrocyanic acid, start to pass in 40g of dry hydrogen chloride gas, control the temperature not to exceed -5°C for 6 hours, filter, and get Iminomethyl ether hydrochloride.

[0026] For the iminomethyl ethyl ether hydrochloride obtained in the previous step, add 85g of ammonium acetate in portions below -5°C and dissolve it in 200ml of absolute ethanol solution, stir vigorously for 1 hour, heat up to room temperature and react for 1 hour, then heat up to 45°C The reaction was continued for 1 hour, and white precipitated ammonium chloride was gradually precipitated, the temperature was lowered, and the mixture was filtered.

[0027] The filtrate is heated to reflux, and at the same time, dry ammonia gas is introduced at a certain speed for 1.5 to 2 hours, and about 35g of ammonia gas is introduced, and white solids are gradually precipitated in the ...

Embodiment 3

[0030] In a 500ml reaction bottle, add 200ml of solvent toluene and 46g of ethanol, stir and cool down to below -10°C, add 27g of hydrocyanic acid, start to pass in 40g of dry hydrogen chloride gas, control the temperature not to exceed 0°C for 6 hours, filter to obtain Aminomethyl ether hydrochloride.

[0031] For the iminomethyl ethyl ether hydrochloride obtained in the previous step, add 78g of ammonium acetate in portions below 0°C and dissolve it in 200ml of absolute ethanol solution, stir vigorously for 1 hour, heat up to room temperature and react for 1 hour, then raise the temperature to 45°C to continue After reacting for 1 hour, white precipitated ammonium chloride gradually precipitated, cooled down, and filtered.

[0032] The filtrate is heated to reflux, and at the same time, dry ammonia gas is introduced at a certain speed for 1.5 to 2 hours, and about 35g of ammonia gas is introduced, and white solids are gradually precipitated in the reaction bottle. After cool...

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Abstract

The invention relates to a synthetic method of 4,6-dihydroxy-pyrimidin, belonging to the field of organic synthesis. In the synthetic method, fatty alcohol, chlorine hydridem, hydrocyanic acid, ammonium acetate and ammonia gas react first. The synthetic method is characterized in that the generated formamidine acetate and alkoxide and malonic ester undergo a ring-closure reaction to generate the 4,6-dihydroxy-pyrimidi. The byproduct hydrocyanic acid is used an initial raw material to prepare the formamidine acetate; and the formamidine acetate and the malonic ester are synthesized to form the 4,6-dihydroxy-pyrimidin. The synthetic method has the advantages of low unit consumption of the raw materials, high yield, low cost of products, fewer three wastes and less pollution to environment.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing 4,6-dihydroxypyrimidine. Background technique [0002] 4,6-dihydroxypyrimidine can be used in the production of medicines and pesticides. In the pharmaceutical industry, it is used to produce intermediates of sulfa drugs sulfamotoxin, vitamin B4, antineoplastic drugs and auxiliary drugs, and can also be used to synthesize formazan 4,6-dichloropyrimidine, an intermediate of the β-methoxyacrylates fungicide azoxystrobin. Already disclosed synthetic techniques, US6096892 (JP2000-510864, ​​CN1214044), US2003 / 0060628 (US6693195, CN1406934, CN1224617), US5847139 (JP10-67755, CN1175576), raw materials are all reacted by formamide, sodium methoxide and malonate , to prepare 4,6-dihydroxypyrimidine. This process is widely used at home and abroad, and the production cost is relatively high. [0003] [0004] WO9708152 (US6248571, JP2000507911, ES2152563, EP08...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/54
Inventor 耿佃云于秀嫒王明贤
Owner YINGKOU YINGXIN CHEM TECH CO LTD
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