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Tinidazole preparing process

A technology for tinidazole and nitroimidazole, which is applied in the field of chemical pharmacy, can solve the problems of numerous raw materials, long production cycle, low yield and the like, and achieve the effects of shortening reaction steps, reducing mass usage and mild reaction conditions

Active Publication Date: 2005-12-14
ZHEJIANG SUPOR PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction steps of this process need four steps, and there are mainly disadvantages such as a large number of raw materials required, large pollution on the operation site, complex process, low yield (total yield is about 40%), long production cycle, and poor product quality.

Method used

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Examples

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preparation example Construction

[0024] 2, the preparation of tinidazole

[0025]

[0026] General Formula IV General Formula I

Embodiment 1

[0028] 1. Add 170g (1.35mol) of 2-methyl-5-nitroimidazole and 106g (1.0mol) of β-hydroxy ethyl sulfide into a 500ml three-necked flask, then add 200ml of xylene, heat up, and heat up at 30 Slowly add 75ml (1.38mol) of concentrated sulfuric acid dropwise at ~55°C for 3-5 hours, then raise the temperature to about 70°C, and keep the reaction at about 70°C for 6 hours. After the heat preservation is completed, the temperature is lowered to below 50°C, the pH of the reaction solution is adjusted to 6.5-7.5 with 20-22% ammonia water, the solid is removed by filtration, the layers are separated, and the organic layer is taken.

[0029] 2. Add 50ml of water and a catalytic amount of ammonium molybdate to the organic layer, raise the temperature to about 65°C and slowly add about 250g of hydrogen peroxide dropwise, keep warm at about 65°C for 3 hours, cool to below 35°C, and filter to obtain about 170g of hydrogen peroxide Tinidazole crude product, the crude product was refined and dr...

Embodiment 2

[0031] 1. Add 170g (1.35mol) of 2-methyl-5-nitroimidazole and 106g (1.0mol) of β-hydroxyethyl sulfide into a 500ml three-necked flask, then add 200ml of o-xylene, heat up, and Slowly add 122ml (2.24mol) of concentrated sulfuric acid dropwise at 40-60°C for 3-5 hours, then raise the temperature to about 70°C, and keep the reaction at about 70°C for 6 hours. After the heat preservation is completed, the temperature is lowered to below 50°C, the pH of the reaction solution is adjusted to 6.5-7.5 with 20-22% ammonia water, the solid is removed by filtration, the layers are separated, and the organic layer is taken.

[0032] 2. Add 50ml of water and a catalytic amount of ammonium molybdate to the organic layer, raise the temperature to about 60°C and slowly add about 250g of hydrogen peroxide dropwise, keep warm at about 60°C for 3 hours, cool to below 35°C, and filter to obtain about 170g of hydrogen peroxide Tinidazole crude product, the crude product was refined and dried with 3...

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Abstract

The present invention is tinidazole preparing process, and belongs to the field of chemically medicine preparing technology. The tinidazole preparing process includes the condensation between beta-hydroxyethylthio ether and2-methyl-5-nitroimidazole as main material in xylene solvent and under the action of Lewis acid; neutralization with alkali solution and water washing to obtain condensate 1-(beta-ethylthioethyl)-2-methyl-5-nitroimidazole; and direct catalytic oxidation of condensate 1-(beta-ethylthioethyl)-2-methyl-5-nitroimidazole under the action of hydrogen peroxide solution and oxidizing catalyst to obtain coarse tinidazole product. Compared with available technology, the present invention has less reaction steps, less pollution, lower production cost, short production period, higher yield and higher product quality.

Description

technical field [0001] The utility model relates to a preparation method of tinidazole {2-methyl-1-[2-(ethylsulfonyl)ethyl]-5-nitro-1H-imidazole}, which belongs to the technical field of chemical pharmacy. Background technique [0002] Tinidazole has a structure as shown in general formula I, and is a highly effective anti-amoeba and anti-anaerobe drug. Compared with the traditional anti-anaerobe drug metronidazole, it has the advantages of good drug effect and small side effects. [0003] [0004] Formula I [0005] Regarding the preparation method of tinidazole, current bibliographical reports generally use β-hydroxyethyl sulfide and 2-methyl-5-nitroimidazole as raw materials, methyl isobutyl ketone as solvent, and condensation reaction under Lewis acid catalysis The condensate 1-(β-ethylthioethyl)-2-methyl-5-nitroimidazole is obtained, and then oxidized with about 30% hydrogen peroxide under acidic conditions to obtain the desired product—tinidazole. The reaction ste...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/91
Inventor 童小兵吕建国姜维斌颜平秋王玮樊友斌杨金女
Owner ZHEJIANG SUPOR PHARM CO LTD
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