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Process for preparing 4-propylthio-o-phenylenediamine

A kind of propylthio-o-phenylenediamine and the technology of preparation steps, which are applied in the field of preparation technology of 4-propylthio-o-phenylenediamine, a key intermediate in the synthesis of albendazole

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

AI Technical Summary

Problems solved by technology

However, due to the reducibility of the propylthio group, it is easy to be reduced by metal catalytic hydrogenation, and it is easy to cause the deactivation of the metal catalyst; in the hydrazine hydrate-ferric chloride reduction method, hydrazine hydrate is flammable and explosive, and the iron sludge formed by the reaction is not easy to filter removal; CO reduction requires high pressure

Method used

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

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Dissolve ammonium chloride (13 g, 0.25 mol) in water (100 mL), add 2-nitro-4-propylthioaniline (21.2 g, 0.1 mol), and slowly add nickel in batches under stirring at 80-90 °C Aluminum alloy (20 g, 0.2 mol). After adding, continue to react at the same temperature, follow the completion of the reaction with thin-layer chromatography, suction filter the reaction mixture while it is hot, and wash the filter residue with a small amount of hot water, cool the filtrate, extract with ethyl acetate, combine the ester layers, wash with water, anhydrous sulfuric acid Sodium drying and rotary evaporation gave 17.4 g of 4-propylthio-o-phenylenediamine with a yield of 95.6%.

Embodiment 2

[0026] Dissolve ammonium chloride (13 g, 0.25 mol) in water (100 mL), add 2-nitro-4-propylthioaniline (21.2 g, 0.1 mol), and slowly add nickel in batches under stirring at 80-90 °C Aluminum alloy (10 g, 0.1 mol). After adding, continue to react at the same temperature, follow the completion of the reaction with thin-layer chromatography, suction filter the reaction mixture while it is hot, and wash the filter residue with a small amount of hot water, cool the filtrate, extract with dichloromethane, combine the organic layers, wash with water, anhydrous sulfuric acid Sodium drying and rotary evaporation gave 17 g of 4-propylthio-o-phenylenediamine with a yield of 93.4%.

Embodiment 3

[0028] Dissolve ammonium chloride (21.8 g, 0.4 mol) in water (100 mL), add 2-nitro-4-propylthioaniline (21.2 g, 0.1 mol), and slowly add nickel in batches under stirring at 80-90 °C Aluminum alloy (20 g, 0.2 mol). After the addition, continue to react at the same temperature, track the completion of the reaction with thin layer chromatography, suction filter the reaction mixture while it is hot, and wash the filter residue with a small amount of hot water, cool the filtrate, extract with chloroform, combine the organic layers, wash with water, and dry over anhydrous sodium sulfate , rotary evaporation, 17.6 g of 4-propylthio-o-phenylenediamine was obtained, and the yield was 96.7%.

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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-4-propylthio phenylamine through being reduced by nickel aluminum alloy and an aqueous solution of ammonium chloride 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

[0001] technical field [0002] 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. [0003] technical background [0004] 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: [0005] 1) Synthetic route using o-nitroaniline as starting material: [0006] [0007] In 1979, it was reported in US4152522 that o-nitroaniline and thiocyanate generated 2-ni...

Claims

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Application Information

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