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Process for preparing albendazole intermediate 4-propylthio-o-phenylenediamine

A technology of propylthio-o-phenylenediamine and preparation steps, which is applied in the field of chemistry or medicinal chemistry, and can solve the problems of hydrazine hydrate being flammable and explosive, restricting the application of preparation technology, etc.

Inactive Publication Date: 2015-09-30
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, hydrazine hydrate is flammable and explosive, the catalysts are mostly precious metals, and there are high-pressure reaction conditions, which restrict the application of this preparation process.

Method used

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  • Process for preparing albendazole intermediate 4-propylthio-o-phenylenediamine
  • Process for preparing albendazole intermediate 4-propylthio-o-phenylenediamine
  • Process for preparing albendazole intermediate 4-propylthio-o-phenylenediamine

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Magnesium metal (14.4 g, 0.6 mol), ammonium sulfate (132 g, 1 mol) and 2-nitro-5-propylthioaniline (21.2 g, 0.1 mol) were added to water (30 mL) and methanol (200 mL ) in a mixed solvent composed of 50°C, stirred and reacted at 50°C, tracked the completion of the reaction with thin-layer chromatography, evaporated the solvent, extracted with ethyl acetate, combined the ester layers, washed with water, dried over anhydrous sodium sulfate, and rotary evaporated to obtain 4-propylthio 17.4 g of o-phenylenediamine, the yield is 95.6%.

Embodiment 2

[0026] Magnesium metal (9.6 g, 0.4 mol), ammonium sulfate (105.6 g, 0.8 mol) and 2-nitro-5-propylthioaniline (21.2 g, 0.1 mol) were added to water (50 mL) and methanol (200 mL ) in a mixed solvent composed of 40°C, stirred and reacted at 40°C, tracked the completion of the reaction by thin-layer chromatography, evaporated the solvent, extracted with dichloromethane, combined the organic layers, washed with water, dried over anhydrous sodium sulfate, and rotary evaporated to obtain 4-propylthio 16.8 g of o-phenylenediamine, the yield is 92.3%.

Embodiment 3

[0028] Metal magnesium (19.2 g, 0.8 mol), ammonium sulfate (158.4 g, 1.2 mol) and 2-nitro-5-propylthioaniline (21.2 g, 0.1 mol) were added to water (40 mL) and ethanol (200 mL ) in a mixed solvent composed of 50°C, stirred and reacted at 50°C, tracked the completion of the reaction with thin-layer chromatography, evaporated the solvent, extracted with chloroform, combined the organic layers, washed with water, dried over anhydrous sodium sulfate, and rotary evaporated to obtain 4-propylthio-phthalic acid Diamine 17.8 g, the yield is 97.8%.

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Abstract

The invention relates to a process for preparing 4-propylthio-o-phenylenediamine. According to the process provided by the invention, 4-propylthio-o-phenylenediamine is prepared from 2-nitro-5-propylthio phenylamine with relatively good stability through being reduced by magnesium metal and ammonium sulfate in an alcohol-water mixed solution under the condition of heating. The process is high in yield, simple in operation and simple and convenient in after-treatment and has a relatively good application prospect.

Description

technical field [0001] The invention belongs to the field of chemistry or medicinal chemistry, and in particular relates to a preparation process of 4-propylthio-o-phenylenediamine, a key intermediate in the synthesis of albendazole. Background technique [0002] Albendazole is a high-efficiency broad-spectrum anthelmintic, which has a significant control effect on pinworms, nematodes, roundworms and other parasites in warm-blooded animals such as dogs and sheep. It can also be used for human cerebral and dermatomyosar cysticercosis. It has low toxicity to human body and animals and little side effects. Since the mid-1970s, there have been many reports about the synthetic route of albendazole at home and abroad, and its existing synthetic route is mainly summarized as follows: [0003] 1) Synthetic route using o-nitroaniline as starting material: [0004] [0005] In 1979, it was reported in US4152522 that o-nitroaniline and thiocyanate generated 2-nitro-4-thiocyanatoa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/36C07C319/20
Inventor 冯润良宋智梅杨凤英刘娜朱文霞
Owner UNIV OF JINAN
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