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Process for preparing 5-nitroimidazole medicine through catalysis of 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: 2020-07-31
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-nitroimidazole medicine through catalysis of small organic molecules
  • Process for preparing 5-nitroimidazole medicine through catalysis of small organic molecules
  • Process for preparing 5-nitroimidazole medicine through catalysis of small organic molecules

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Add 127.1 g of 2-methyl-5-nitroimidazole, 635.5 g of ethyl acetate, and 4.13 g of catalyst to the reaction flask. Stir and mix evenly. The stirring speed is 50~300rpm.

[0056] Add 127.1 g of epichlorohydrin to the above reaction flask,

[0057] Control the temperature in the reaction flask to 25~30℃, stir the reaction for 6 hours, and stir at 50~300rpm;

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

[0059] Adjust the pH value of the aqueous phase to about 8.0 with 1.25 mol / L sodium hydroxide solution, and solids will precipitate out. After suction filtration, the solid phase is rinsed with a small amount of water and dried to obtain the catalyst, which can be directly applied.

[0060] The organic phase is washed with water 1 times the weight of 2-methyl-5-nitroimidazole, separated into lay...

Embodiment 2

[0064] Add 127.1 g of 2-methyl-5-nitroimidazole, 1271.0 g of butyl acetate, and 6.3 g of catalyst to the reaction flask. Stir and mix evenly. The stirring speed is 50~300rpm.

[0065] Add 139.0 g of epichlorohydrin to the above reaction flask,

[0066] Control the temperature in the reaction flask at 20~35℃, stir the reaction for 8 hours, and stir at 50~300rpm;

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

[0068] The pH of the aqueous phase is adjusted to about 10 with 2.5 mol / L sodium hydroxide solution, and solids are separated out, filtered with suction, the solids are rinsed with a small amount of water, dried to obtain the catalyst, which can be directly applied.

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

Embodiment 3

[0072] Add 127.1 g of 2-methyl-5-nitroimidazole, 635.5 g of ethyl acetate, and 4.13 g of catalyst to the reaction flask, stir and mix well, at a stirring speed of 50~300 rpm,

[0073] Add 115.6 g of propylene oxide to the above reaction flask,

[0074] Control the temperature in the reaction flask to 25~30℃, stir the reaction for 6 hours, and stir at 50~300rpm;

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

[0076] The pH of the aqueous phase is adjusted to about 8 with 1.25 mol / L sodium hydroxide solution, and solids are precipitated. After suction filtration, the solids are rinsed with a small amount of water and dried to obtain the catalyst, which can be used directly.

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

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PUM

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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 particularly relates to a process for catalyzing and synthesizing 5-nitroimidazole drugs by using small bifunctional organic molecules as a catalyst. Background technique [0002] 5-Nitroimidazole drugs have obvious antibacterial activity, and can also be anti-tuberculosis, anti-parasitic, anti-virus and anti-tumor sensitizers. At present, many drugs are used in clinical practice. The main varieties of 5-nitroimidazole antibiotics are metronidazole, dimenidazole, lonidazole, 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 highly effective anti-anaerobes, anti-trichomoniasis and anti-amoeba activities. Compared with traditional nitroimidazole dr...

Claims

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Application Information

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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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