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Method for preparing fenbendazole intermediate 2-nitro-4-thiophenyl aniline

A technology of phenylthioaniline and nitrogen phenylthioacetanilide, which is applied in the field of organic synthesis of fenbendazole, can solve the problems of high corrosion resistance requirements of reaction equipment, impact on economic benefits, high reaction temperature, etc., and achieve low production cost, The effect of low equipment investment and short steps

Active Publication Date: 2020-08-07
SHANDONG GUOBANG PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, DMF is used as the solvent during condensation in this route, the reaction temperature is high, and the corrosion resistance requirements of the reaction equipment are high.
[0006] The preparation method of 2-nitro-4-phenylthioaniline disclosed in the above patent still needs to be further improved in the application of large-scale industrial production, and there are problems of complicated operation and poor yield, thus affecting economic benefits

Method used

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  • Method for preparing fenbendazole intermediate 2-nitro-4-thiophenyl aniline
  • Method for preparing fenbendazole intermediate 2-nitro-4-thiophenyl aniline
  • Method for preparing fenbendazole intermediate 2-nitro-4-thiophenyl aniline

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Effect test

Embodiment 1

[0027] Add 120g of acetonitrile, 30g of thiophenol, 10.12g of triethylamine, and 39.18g of N-chloroacetanilide into a 250ml four-necked bottle, heat up to 70°C, and keep it warm for 7 hours to undergo condensation reaction; then add 31.91g of o-nitroaniline , after a substitution reaction at 85°C for 12 hours, 2-nitro-4-phenylthioaniline was generated, and 57.29 g of fenbendazole intermediate 2-nitro-4-phenylthioaniline was isolated with a yield of 85.42% .

Embodiment 2

[0029] Add 120g of acetonitrile, 30g of thiophenol, 10.12g of triethylamine, and 44.78g of N-chloroacetanilide into a 250ml four-neck flask, heat up to 70°C, and keep it warm for 7 hours to undergo condensation reaction; then add 31.91g of o-nitroaniline , after a substitution reaction at 85°C for 12 hours, 2-nitro-4-phenylthioaniline was generated, and 57.75 g of fenbendazole intermediate 2-nitro-4-phenylthioaniline was isolated with a yield of 86.11% .

Embodiment 3

[0031] Add 120g of acetonitrile, 30g of thiophenol, 10.12g of triethylamine, and 41.05g of N-chloroacetanilide into a 250ml four-necked bottle, heat up to 70°C, and keep it warm for 7 hours to undergo condensation reaction; then add 31.91g of o-nitroaniline , after a substitution reaction at 85°C for 12 hours, 2-nitro-4-phenylthioaniline was generated, and 57.51 g of fenbendazole intermediate 2-nitro-4-phenylthioaniline was isolated with a yield of 85.75% .

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Abstract

The invention discloses a method for preparing a fenbendazole intermediate 2-nitro-4-thiophenyl aniline, and solves the problems that the existing preparation method is unreasonable; and the technicalproblems of high raw material price, complex operation, high reaction equipment condition requirements, high cost, poor yield and unsuitability for industrial production exist in the prior art can besolved. The invention relates to a method for preparing a fenbendazole intermediate 2-nitro-4-thiophenyl aniline. Under the substitution reaction conditions, substitution reaction is carried out on the N-phenylthio acetanilide and o-nitroaniline, thus synthesizing the fenbendazole intermediate 2-nitro-4-thiophenyl aniline; the whole novel synthesis method is mild in reaction conditions, the operation is simple and convenient, the safety is high, the product yield is high, the atom utilization rate is high, the three wastes are few, the operation is simple and convenient, the cost is low, thesustainable development requirements are met, and the method is suitable for industrial production; the method can be widely applied to the technical field of fenbendazole organic synthesis.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis of fenbendazole, in particular to a method for preparing fenbendazole intermediate 2-nitro-4-phenylthioaniline. Background technique [0002] Fenbendazole, also known as benzimidazole, chemically named 5-phenylthiobenzimidazole-2-methyl carbamate, is a benzimidazole anthelmintic. It not only has high anthelmintic activity against adults and larvae of gastrointestinal nematodes, but also has good effects on Dictyocaulus, Fasciola and tapeworm, and has a strong effect on killing insect eggs. It has the advantages of maggot spectrum light, low toxicity, good tolerance, wide safety range and good palatability. [0003] Existing fenbendazole traditional technology is to take m-chloroaniline as raw material, through acylation, nitration, condensation to prepare 2-nitro-4-phenylthioaniline, and then through reduction, cyclization reaction to prepare fenbendazole, Although the current industri...

Claims

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Application Information

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IPC IPC(8): C07C323/37C07C319/14
CPCC07C319/14C07C313/28C07C323/37
Inventor 王兴国乔建超程贺王友杰刘聪
Owner SHANDONG GUOBANG PHARMA
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