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Method for synthesizing secnidazole and secnidazole

A technology for synthesizing secnidazole and secnidazole, which is applied in organic chemistry and other fields, can solve problems such as high reaction temperature and acid waste gas corrosion, and achieve the effects of short reaction time, reduced corrosion, and reduced energy consumption

Active Publication Date: 2014-05-07
HUNAN DINUO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The present invention aims to provide a method for synthesizing secnidazole and secnidazole to solve the problems of high reaction temperature and generated acid waste gas that will corrode equipment in the existing secnidazole synthesis process

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] This embodiment provides a method for synthesizing secnidazole, comprising the following steps:

[0031] Add 2-methyl-5-nitroimidazole, 1-bromo-2-propanol, potassium carbonate, and acetone at a molar ratio of 1:2:2.1:14 into a 10L glass reactor, in which 2-methyl- The mass of 5-nitroimidazole is 635g, the mass of 1-bromo-2-propanol is 1380g, the mass of potassium carbonate is 1480g, and the volume of acetone is 5L.

[0032] Under the condition of stirring, the reaction was refluxed for 4 hours, and the reaction temperature was 60°C; according to the TLC detection (developing condition: GF254 silica gel plate, developing agent chloroform: ethanol = 85:15) the reaction termination point, the reaction mixture A was obtained.

[0033] Recover the acetone in the reaction mixture A to obtain the reaction mixture B; add 6L of water to the reaction mixture B, cool the reaction mixture B to 3°C, and centrifuge to obtain a wet product; stir and wash the wet product with water at a ...

Embodiment 2

[0037] This embodiment provides a method for synthesizing secnidazole, comprising the following steps:

[0038] Add 2-methyl-5-nitroimidazole, 1-bromo-2-propanol, potassium carbonate, and acetone at a molar ratio of 1:3:3:20 into a 10L glass reactor, in which 2-methyl- The mass of 5-nitroimidazole is 635g, the mass of 1-bromo-2-propanol is 2070g, the mass of potassium carbonate is 2114g, and the volume of acetone is 7.1L.

[0039] Under the condition of stirring, reflux reaction for 5 hours, the reaction temperature is 70°C; according to the TLC detection (development condition: GF254 silica gel plate, developer chloroform: ethanol = 85:15) the reaction termination point, the reaction mixture A was obtained.

[0040] Recover the acetone in the reaction mixture A to obtain the reaction mixture B; add 9L of water to the reaction mixture B, cool the reaction mixture B to 0°C, and centrifuge to obtain a wet product; stir and wash the wet product with water at a temperature of 1°C ...

Embodiment 3

[0044] This embodiment provides a method for synthesizing secnidazole, comprising the following steps:

[0045] Add 2-methyl-5-nitroimidazole, 1-bromo-2-propanol, potassium carbonate, and acetone at a molar ratio of 1:1.5:2:7 into a 10L glass reactor, in which 2-methyl- The mass of 5-nitroimidazole is 635g, the mass of 1-bromo-2-propanol is 1035g, the mass of potassium carbonate is 1410g, and the volume of acetone is 2.5L.

[0046] Under the condition of stirring, reflux reaction for 3 hours, the reaction temperature is 70°C; according to the TLC detection (development condition: GF254 silica gel plate, developer chloroform: ethanol = 85:15) the reaction termination point, the reaction mixture A was obtained.

[0047] Recover the acetone in the reaction mixture A to obtain the reaction mixture B; add 3L of water to the reaction mixture B, and cool the reaction mixture B to 2°C, centrifuge to obtain a wet product; stir and wash the wet product with water at a temperature of 2°C...

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PUM

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Abstract

The invention discloses a method for synthesizing secnidazole and secnidazole. According to the method, 2-methyl-5-nitroimidazole and 1-bromine-2-propyl alcohol serve as raw materials, acetone serves as a solvent, and potassium carbonate or sodium carbonate serves as a catalyst. The method comprises the following steps: mixing 2-methyl-5-nitroimidazole, 1-bromine-2-propyl alcohol, the catalyst and acetone, carrying out a reflux reaction, and obtaining a reaction mixture A after the reaction is ended; separating and purifying the reaction mixture A, and obtaining the secnidazole. According to the method, 2-methyl-5-nitroimidazole and 1-bromine-2-propyl alcohol serve as the raw materials, acetone serves as the solvent, and the potassium carbonate or sodium carbonate serves as the catalyst, so that secnidazole is synthesized, strong acids are avoided, and the corrosion to the equipment and pipeline system is reduced. Moreover, the reaction temperature is low, and the reaction time is short, so that the energy consumption is reduced.

Description

technical field [0001] The invention relates to the technical field of chemical pharmacy, in particular to a method for synthesizing secnidazole and secnidazole. Background technique [0002] Secnidazole, chemical name: l-(2-hydroxypropyl)-2-methyl-5-nitroimidazole, and metronidazole, ornidazole, tinidazole belong to 5-nitroimidazoles Antiprotozoal and anaerobic drugs. Secnidazole has anti-anaerobic bacteria, Helicobacter pylori, Giardia, intestinal amoebiasis and other trichomonas and flagellates parasitic in the cavity, and mainly acts on the growth period of protozoa or anaerobic bacteria , destroy DNA strands or inhibit DNA synthesis, leading to the death of protozoa and anaerobic bacteria; it has a strong killing effect on trichomonas in genitourinary organs, amoeba and giardia in intestinal tract and tissues. [0003] At present, the existing synthesis process of secnidazole is: under the condition of strong acid or strong alkali, reacting 2-methyl-5 nitroimidazole w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/94
CPCC07D233/94
Inventor 曾永锋易志恒
Owner HUNAN DINUO PHARMA