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Synthetic method for 2-cyano-4-chloro-5-(4-methylphenyl)imidazole

A technology of methyl phenyl and synthetic method, which is applied in the field of synthesis of 2-cyano-4-chloro-5-(4-methylphenyl) imidazole, which can solve the difficulty of industrial production and the safety hazards of industrial production High, difficult operation and other problems, to achieve the effect of high product yield, short reaction time, easy process operation

Active Publication Date: 2015-12-09
RUDONG ZHONGYI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] The raw material ethylenedicyanide is highly toxic gas, the operation is difficult, the safety risk of industrial production is high, and the industrial production is difficult

Method used

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  • Synthetic method for 2-cyano-4-chloro-5-(4-methylphenyl)imidazole
  • Synthetic method for 2-cyano-4-chloro-5-(4-methylphenyl)imidazole
  • Synthetic method for 2-cyano-4-chloro-5-(4-methylphenyl)imidazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) In the light reactor, add 300L cyclohexane, 135Kg p-methyl acetophenone and 50L hydrogen peroxide, turn on the light, add 170Kg bromine dropwise, the reaction temperature is 20°C, add dropwise for 1 hour, at 20°C Keep it warm for 3 hours, cool and crystallize in an ice bath, and filter with suction to obtain compound Ⅰ;

[0035] (2) In reactor A, add 500L dimethyl sulfoxide and 215Kg compound I, and stir and react at 120°C for 4 hours. After the reaction is completed, cool and crystallize in an ice bath, and obtain compound II by suction filtration;

[0036] (3) In reactor B, add 800L of methanol, 135Kg of glyoxal, 325Kg of hydroxylamine sulfate and 129Kg of compound II, heat up to reflux and keep it warm for 6 hours, the raw materials are completely reacted, crystallized by ice bath cooling, washed with water, and suction filtered to obtain Compound III;

[0037] (4) In reactor C, add 600Kg N,N-dimethylformamide and 188Kg compound III, cool in an ice bath, add 136...

Embodiment 2

[0039] (1) In the light reactor, add 500L cyclohexane, 155Kg p-methyl acetophenone and 70L hydrogen peroxide, turn on the light, add 190Kg bromine dropwise, the reaction temperature is 30°C, add dropwise for 1 hour, at 30°C Keep it warm for 3 hours, cool and crystallize in an ice bath, and filter with suction to obtain compound Ⅰ;

[0040] (2) In reactor A, add 500L dimethyl sulfoxide and 200Kg compound I, stir and react at 120°C for 4 hours, after the reaction is completed, cool and crystallize in an ice bath, and obtain compound II by suction filtration;

[0041] (3) In reactor B, add 800L of methanol, 145Kg of glyoxal, 365Kg of hydroxylamine sulfate and 140Kg of compound II, heat up to reflux and keep it warm for 6 hours, the raw materials are completely reacted, crystallized by ice bath cooling, washed with water, and suction filtered to obtain Compound III;

[0042] (4) In reactor C, add 700Kg N,N-dimethylformamide and 200Kg compound III, cool in an ice bath, add 156Kg t...

Embodiment 3

[0044] (1) In the light reactor, add 300L cyclohexane, 155Kg p-methyl acetophenone and 75L hydrogen peroxide, turn on the light, add 190Kg bromine dropwise, the reaction temperature is 20°C, add dropwise for 1 hour, at 20°C Keep it warm for 3 hours, cool and crystallize in an ice bath, and filter with suction to obtain compound Ⅰ;

[0045] (2) In reactor A, add 500L dimethyl sulfoxide and 228Kg compound I, and stir and react at 110°C for 4 hours. After the reaction is completed, cool and crystallize in an ice bath, and obtain compound II by suction filtration;

[0046] (3) In reactor B, add 800L of methanol, 115Kg of glyoxal, 305Kg of hydroxylamine sulfate and 109Kg of compound II, heat up to reflux and keep it warm for 6 hours, the raw materials are completely reacted, cooled in an ice bath to crystallize, washed with water, and suction filtered to obtain Compound III;

[0047] (4) In reactor C, add 600Kg N,N-dimethylformamide and 168Kg compound III, cool in an ice bath, add...

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Abstract

The invention relates to a synthetic method for 2-cyano-4-chloro-5-(4-methylphenyl)imidazole. The synthetic method comprises the following steps: (1) by taking p-methylacetophenone as a raw material, carrying out a halogenating reaction under a light condition to obtain a compound I; (2) dissolving the obtained compound I in a solvent, stirring the mixture to react at a certain temperature, and performing cooling and suction-filtering to obtain a compound II; (3) dissolving the obtained compound II in a solvent and carrying out a reaction with glyoxal and hydroxylamine sulphate at a certain temperature to obtain a compound III; and (4) dissolving the obtained compound III in a solvent, carrying out a reaction with sulfoxide chloride in an ice bath in a manner of raising the temperature to room temperature and keeping the temperature for the reaction, dropwise adding sulfur chloride, and after reaction, washing the product to obtain a compound IV which is 2-cyano-4-chloro-5-(4-methylphenyl)imidazole. The synthetic method is good in atom economy, simple and convenient in process operation and high in product yield and industrial application value.

Description

technical field [0001] The invention relates to a method for synthesizing a key intermediate of Cyazofamida, in particular to a method for synthesizing 2-cyano-4-chloro-5-(4-methylphenyl)imidazole. Background technique [0002] Cyazofamid is a new generation of imidazole fungicide developed by Ishihara Co., Ltd. of Japan and jointly developed with BASF. It is the first agricultural fungicide that acts on the mitochondrial electron transfer complex IIIQi. Specific drugs for oomycete diseases represented by mildew and blight. Cyazofim has very low toxicity and good environmental compatibility. Cyazofamid is a promising fungicide for oomycete diseases. The development and use of Cyazofim has great social and economic benefits. [0003] Regarding 2-cyano-4-chloro-5-(4-methylphenyl)imidazole, its chemical formula is: C 11 h 8 ClN 3 ; The structural formula is: [0004] [0005] The synthesis of the key intermediate of Cyazofamida mainly has the following three routes in ...

Claims

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Application Information

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IPC IPC(8): C07D233/90
CPCC07D233/90
Inventor 袁绍志董建生叶振君戴乙徐王正荣朱峰王海涛
Owner RUDONG ZHONGYI CHEM
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