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Preparation method of 2-amino-5-phenylthio-(2-methoxy)acetanilide

A technology of phenylthioaniline and acetanilide, which is applied in the field of preparation of 2-amino-5-phenylthio-acetanilide, can solve problems such as inconvenient production and operation, large environmental pollution, and lack of economic value, and reduce equipment and The requirements of operating conditions, the reduction of waste disposal costs, and the effect of improving safety and stability

Active Publication Date: 2018-07-20
珠海优润医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods are gradually phased out due to heavy environmental pollution and inconvenient production operations, or cannot be applied on a large scale due to high energy consumption and demanding equipment requirements, or have limited application range due to expensive catalysts and lack of economic value due to easy poisoning.

Method used

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  • Preparation method of 2-amino-5-phenylthio-(2-methoxy)acetanilide
  • Preparation method of 2-amino-5-phenylthio-(2-methoxy)acetanilide
  • Preparation method of 2-amino-5-phenylthio-(2-methoxy)acetanilide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] (1) Preparation of 2-nitro-5-phenylthioaniline: add 2-nitro-5-mercaptoaniline (17.0g) in the 250ml reaction flask equipped with thermometer, water separator, condenser and stirring device , Potassium Carbonate (13.8g) and Chlorobenzene (85.0g), nitrogen replacement three times, heated to 130-135°C, stirred and refluxed for 3-5 hours; filtered while hot, stirred and cooled the filtrate to 0-5°C, and then continued Stir for 1 hour, filter and collect the precipitated crystals, wash and dry to obtain 2-nitro-5-phenylthioaniline with a yield of 95.4%;

[0038] (2) Preparation of 2-nitro-5-phenylthio-(2-methoxy)acetanilide: add 2-nitro-5-benzene to a 500ml reaction bottle equipped with a thermometer, condenser and stirring device Thioaniline (24.7g) and methyl 2-methoxyacetate (123.0g) were replaced by nitrogen three times, stirred and heated to 120-130°C for 5-7 hours; the temperature was lowered to below 70°C, and n-hexane ( 200ml) and cooled to 0-5°C, continued to stir f...

Embodiment 2

[0041] (1) Preparation of 2-nitro-5-phenylthioaniline: add 2-nitro-5-mercaptoaniline (85.0g) in the 1000ml reaction flask equipped with thermometer, water separator, condenser and stirring device , Potassium carbonate (69.1g) and bromobenzene (340.0g), replaced by nitrogen three times, stirred and refluxed at 150-160°C for 5-6 hours; filtered while hot, stirred and cooled the filtrate to -5-0°C, continued Stir for 1 hour, filter and collect the precipitated crystals, wash and dry to obtain 2-nitro-5-phenylthioaniline with a yield of 94.3%.

[0042](2) Preparation of 2-nitro-5-phenylthio-(2-methoxy)acetanilide: add 2-nitro-5-benzene to a 2000ml reaction flask equipped with a thermometer, condenser and stirring device Thioaniline (123.1g) and methyl 2-methoxyacetate (500.0g), replaced by nitrogen three times, stirred and heated to 110-120°C for 8-10 hours; cooled to below 70°C, added n-heptane dropwise (1000ml) after cooling down to 0~5°C, continue to stir for 1 hour, filter, c...

Embodiment 3

[0045] (1) Preparation of 2-nitro-5-phenylthioaniline: add 2-nitro-5-mercaptoaniline (17.0g) in the 500ml reaction flask equipped with thermometer, water separator, condenser and stirring device , Potassium carbonate (27.5g) and chlorobenzene (170.0g), replaced by nitrogen three times, heated to 130-135°C, stirred and refluxed for 3-5 hours; filtered while hot, stirred and cooled the filtrate to -20--10°C, Stirring was continued for another 1 hour, the precipitated crystals were collected by filtration, washed and dried to obtain 2-nitro-5-phenylthioaniline with a yield of 89.5%;

[0046] (2) Preparation of 2-nitro-5-phenylthio-(2-methoxy)acetanilide: add 2-nitro-5-benzene to a 250ml reaction bottle equipped with a thermometer, condenser and stirring device Thioaniline (24.7g) and methyl 2-methoxyacetate (50.0g) were replaced by nitrogen three times, stirred and heated to 120-130°C for 5-7 hours; the temperature was lowered to below 70°C, and n-hexane ( 50ml) and cooled to 0-...

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Abstract

The invention belongs to the technical field of organic synthesis and particularly relates to a preparation method of 2-amino-5-phenylthio-(2-methoxy)acetanilide. According to the method, 2-nitro-5-(phenylthio)aniline is prepared from 2-nitro-5-mercaptoaniline and benzene halide and then subjected to a reaction with methyl methoxyacetate, 2-nitro-5-phenylthio-(2-methoxy)acetanilide is generated and subjected to catalytic hydrogenation reduction finally, and the target product is obtained. The preparation method has good reaction selectivity, and the obtained target product is high in purity and yield; use of high-toxicity materials is avoided, requirements for equipment and operation conditions are reduced, and safety and stability of the preparation method are improved; doses of the reaction materials are optimized, and excess benzene halide and methyl methoxyacetate can be recycled after being recovered simply; little solid waste is produced, waste treatment cost is reduced greatly,and the requirement for environmental protection is met.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 2-amino-5-phenylthio-(2-methoxy)acetanilide. Background technique [0002] Febantyr is a veterinary anthelmintic, which can be used to drive away various nematodes, adults and larvae in dogs, sheep, pigs, horses and other animals. Febantel itself does not have anthelmintic activity, but exerts anthelmintic effect through conversion into fenbendazole, fenbendazole sulfoxide and oxfendazole sulfone in animals. The role and application of febantyr are the same as fenbendazole, which has a strong affinity for tubulin in worms in structure, and is significantly higher than the affinity for mammalian tubulin, so it can prevent microtubule Aggregates and destroys the transport system of absorbing cells, and finally activates various lysosomal enzymes (Iysosomal enzymes) to cause incomplete absorption and digestion of nutrient particles, so ...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C323/37C07C319/20C07C323/41
CPCC07C319/14C07C319/20C07C323/37C07C323/41
Inventor 付长安左斌海柯兴斌崔薛文周珊珊
Owner 珠海优润医药科技有限公司
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