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Process for preparing 5-nitroimidazoles by catalyzing small organic molecules

A technology of nitroimidazoles and small molecule catalysis, which is applied in the fields of organic chemistry, organic compound/hydride/coordination complex catalyst, chemical/physical process, etc. The problem of large amount of three wastes is achieved to solve the effect of large equipment corrosion, high conversion rate and selectivity, and small usage

Active Publication Date: 2020-09-29
湖南九典宏阳制药有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The invention provides a process for catalytically synthesizing 5-nitroimidazoles by using bifunctional small organic molecules as catalysts to solve the problem of traditional preparation of 5-nitroimidazoles (ornidazole, secnidazole). Equivalent or even a large excess of highly corrosive, large amount of three wastes and difficult to handle catalysts, there are technical problems such as low reaction conversion rate, large amount of three wastes and difficult to handle

Method used

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  • Process for preparing 5-nitroimidazoles by catalyzing small organic molecules
  • Process for preparing 5-nitroimidazoles by catalyzing small organic molecules
  • Process for preparing 5-nitroimidazoles by catalyzing small organic molecules

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] In reaction flask, add 127.1 g 2-methyl-5-nitroimidazole, 635.5 g ethyl acetate, 4.13 g catalyzer, stir and mix evenly, stirring speed is 50~300rpm,

[0056] In above-mentioned reaction bottle, add 127.1 g epichlorohydrin,

[0057] Control the temperature in the reaction bottle to 25~30°C, stir the reaction for 6 hours, and the stirring speed is 50~300rpm;

[0058] After the reaction, add water that is 1 times the weight of 2-methyl-5-nitroimidazole (127.1g), adjust the pH to about 4.0 with 1 mol / L hydrochloric acid, stand and separate to obtain the organic phase and water Mutually;

[0059] The pH value of the water phase was adjusted to about 8.0 with 1.25 mol / L sodium hydroxide solution, solids were precipitated, filtered with suction, the solid phase was rinsed with a small amount of water, and dried to obtain a catalyst, which could be used directly.

[0060] The organic phase was washed with water 1 times the weight of 2-methyl-5-nitroimidazole, layered, dried o...

Embodiment 2

[0064] In reaction flask, add 127.1 g 2-methyl-5-nitroimidazole, 1271.0 g butyl acetate, 6.3 g catalyzer, stir and mix evenly, stirring speed is 50~300rpm,

[0065] In above-mentioned reaction bottle, add 139.0 g epichlorohydrin,

[0066] Control the temperature in the reaction bottle to 20~35°C, stir the reaction for 8 hours, and the stirring speed is 50~300rpm;

[0067] After the reaction is over, add water (127.1 g) that is 1 times the weight of 2-methyl-5-nitroimidazole, adjust the pH to about 5.5 with 2 mol / L hydrochloric acid, let stand and separate to obtain the aqueous phase and the organic phase. Mutually;

[0068] Use 2.5 mol / L sodium hydroxide solution to adjust the pH value of the aqueous phase to about 10. Solids are precipitated, filtered with suction, rinsed with a small amount of water, and dried to obtain a catalyst, which can be used directly.

[0069] The organic phase was washed with water 1 times the weight of 2-methyl-5-nitroimidazole (127.1g), separate...

Embodiment 3

[0072] In reaction flask, add 127.1 g 2-methyl-5-nitroimidazole, 635.5 g ethyl acetate, 4.13 g catalyzer, stir and mix evenly, stirring speed is 50~300 rpm,

[0073] Add 115.6 g propylene oxide in above-mentioned reaction bottle,

[0074] Control the temperature in the reaction bottle to 25~30°C, stir the reaction for 6 hours, and the stirring speed is 50~300rpm;

[0075] After the reaction, add water that is 1 times the weight of 2-methyl-5-nitroimidazole (127.1g), adjust the pH to about 4 with 1 mol / L hydrochloric acid, let stand and separate to obtain the organic phase and water Mutually;

[0076] The pH of the water phase was adjusted to about 8 with 1.25 mol / L sodium hydroxide solution. Solids were precipitated, filtered with suction, rinsed with a small amount of water, and dried to obtain a catalyst, which could be used directly.

[0077] The organic phase was washed with water 1 times the weight of 2-methyl-5-nitroimidazole (127.1g), separated, dried over anhydrous s...

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Abstract

The invention provides a process for preparing a 5-nitroimidazole medicine through catalysis of small organic molecules. The preparation method comprises the following steps: 1) uniformly stirring andmixing 2-methyl-5-nitroimidazole, a solvent and a catalyst which is selected from 1-(3, 5-ditrifluoromethyl phenyl)-3-(2-dimethylamino-cyclohexyl)-thiourea, and 2) adding epoxy chloropropane or epoxypropane into a reaction system in the step 1), and reacting to obtain the 5-nitroimidazole medicine. According to the present invention, the 5-nitroimidazole medicine prepared by using the synthesisprocess has characteristics of low catalyst consumption, high catalytic activity, high reaction selectivity, high yield, easy catalyst recycling, and environmental protection.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a process for catalytically synthesizing 5-nitroimidazole drugs by using bifunctional small organic molecules as catalysts. Background technique [0002] 5-nitroimidazoles have obvious antibacterial activity, and can also be used as anti-tuberculosis, anti-parasite, anti-virus and anti-tumor sensitizers. Many drugs have been used clinically. The main varieties of 5-nitroimidazole antibacterial drugs are metronidazole, demetonidazole, ronidazole, tinidazole, ornidazole and secnidazole. Among them, metronidazole, tinidazole, and ornidazole are the first, second, and third-generation anti-anaerobic drugs used in clinical practice. Secnidazole is a newly developed 5-nitroimidazole antibacterial drug. [0003] Ornidazole and secnidazole have high-efficiency anti-anaerobe, anti-trichomonas and anti-amoeba activities. Compared with traditional nitroimidazoles suc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/94B01J31/02
CPCB01J31/0245B01J31/0271C07D233/94Y02P20/584
Inventor 胡矿谭军华郑霞辉
Owner 湖南九典宏阳制药有限公司
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