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Method for synthesizing 2-methyl-5-nitroimidazole-1-ethanol

A technology of nitroimidazole and methyl is applied in the field of synthesizing 2-methyl-5-nitroimidazole-1-ethanol, and can solve the problem of low reaction efficiency of a kettle type reactor, large consumption of formic acid and sodium hydroxide, and production cost. Low and other problems, to achieve the effect of high reaction efficiency and finished product conversion rate, lower production cost, and less material back-mixing

Active Publication Date: 2012-01-18
HUBEI HONGYUAN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The conversion rate of 2-methyl-5-nitroimidazole and the final product 2-methyl-5-nitroimidazole- The yield of 1-ethanol is low, consumption of formic acid and sodium hydroxide amount is large, production cost is high, and the defect and the deficiency that the reaction efficiency of tank reactor is low, provide a kind of synthetic 2-methyl-5-nitroimidazole- The method of 1-ethanol, using a mixed solution of formic acid and sulfuric acid as a solvent, significantly increased the conversion rate of 2-methyl-5-nitroimidazole and the final product 2-methyl-5-nitroimidazole-1-ethanol The yield rate is high, and the consumption of formic acid and sodium hydroxide is less, the production cost is low, and the reaction equipment adopts a tubular reactor, and the reaction efficiency is high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In a 500ML stirred tubular circulating reactor, add 52 parts of formic acid with a mass concentration of 70%, dropwise add 35 parts of sulfuric acid with a mass concentration of 95%, control the temperature below 20°C, and then add 80 parts of 2-methyl -5-nitroimidazole, configured as a mixed solution, and the mixed solution was slowly heated to 72°C. Then add ethylene oxide and mass concentration to the reactor alternately and be the sulfuric acid of 95%, the ethylene oxide addition is respectively: 18,10,14 and 12 parts, the sulfuric acid addition is respectively 6,3 and 2.5 parts. After the alternate addition, keep the temperature of the reactor at 72°C, 2-methyl-5-nitroimidazole reacts with ethylene oxide to generate 2-methyl-5-nitroimidazole-1-ethanol, and the reaction time is 5 hours. Then cool down the reacted solution to room temperature, add an appropriate amount of water, stir, and add sodium hydroxide to adjust the pH to 5. Then the solution was cooled to ro...

Embodiment 2

[0025] In a 500ML stirred tubular circulating reactor, add 43 parts of formic acid with a mass concentration of 98%, dropwise add 38 parts of sulfuric acid with a mass concentration of 90%, control the temperature below 20°C, and then add 80 parts of 2-methyl -5-nitroimidazole, configured as a mixed solution, and the mixed solution was slowly heated to 85°C. Then alternately add ethylene oxide and mass concentration to the reactor and be 90% sulfuric acid, the ethylene oxide addition is respectively: 20, 12, 14 and 9 parts, the sulfuric acid addition is respectively 4, 4 and 2 parts. After the alternate addition, keep the temperature of the reactor at 85°C, and react 2-methyl-5-nitroimidazole with ethylene oxide to generate 2-methyl-5-nitroimidazole-1-ethanol, and the reaction time is 2.5 hours. Then cool down the reacted solution to room temperature, add an appropriate amount of water, stir, and adjust the pH value to 3.5 with sodium hydroxide. Then the solution was cooled t...

Embodiment 3

[0027] In a 500ML stirred tubular circulating reactor, add 46 parts of formic acid with a mass concentration of 88%, dropwise add 30 parts of sulfuric acid with a mass concentration of 98%, control the temperature below 20°C, and then add 80 parts of 2-methyl -5-nitroimidazole, configured as a mixed solution, and the mixed solution was slowly heated to 108°C. Then alternately add ethylene oxide and mass concentration to the reactor to be 98% sulfuric acid, the ethylene oxide addition is respectively: 20, 12, 14 and 9 parts, the sulfuric acid addition is respectively 4, 4 and 2 parts. After the alternate addition, the temperature of the reactor was kept at 108° C., and 2-methyl-5-nitroimidazole reacted with ethylene oxide to generate 2-methyl-5-nitroimidazole-1-ethanol. The reaction time was 3.5 hours. Then cool down the reacted solution to room temperature, add an appropriate amount of water, stir, and add sodium hydroxide to adjust the pH value to 4. Then the solution was co...

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Abstract

The invention provides a method for synthesizing 2-methyl-5-nitroimidazole-1-ethanol, which comprises the following steps: the mixed solution of 2-methyl-5-nitroimidazole, formic acid and sulfuric acid is prepared according to the mole ratio of 1:0.5-0.7:1.2-1.7; ethylene oxide and concentrated sulfuric acid with the mole ratio of 1:0.08-0.3 are alternately added into the mixed solution for 3-4 times; the reaction temperature is 72-108 DEG C, the reaction time is 2.5-5 hours, and after reaction, sodium hydroxide is added to regulate the PH value of the solution to 9.5-10.5, and a finished product is precipitated through crystallization; and a 2-methyl-5-nitroimidazole-1-ethanol finished product is obtained through purification. In the method for synthesizing 2-methyl-5-nitroimidazole-1-ethanol provided by the invention, the mixed solution of formic acid and sulfuric acid is used as a solvent, the conversion rate and the yield are obviously improved, formic acid and sodium hydroxide consumption is less, and the production cost is low.

Description

technical field [0001] The invention relates to a method for synthesizing 2-methyl-5-nitroimidazole-1-ethanol, belonging to the technical field of organic chemistry. Background technique [0002] 2-Methyl-5-nitroimidazole-1-ethanol (also known as metronidazole) is an antibiotic raw material widely used in the pharmaceutical and chemical industry. It has a strong antibacterial effect on most anaerobic bacteria, and its antibacterial spectrum includes fragile Bacteroides and other Bacteroides, Fusobacterium, Clostridium perfringens, Eubacterium, Veillonella, Peptococcus and Peptostreptococcus, etc. At the same time, 2-methyl-5-nitroimidazole-1-ethanol can also be used as a raw material for the production of benzoyl metronidazole, tinidazole and other drugs, and has a wide range of uses. [0003] 2-methyl-5-nitroimidazole-1-ethanol is usually synthesized from 2-methyl-5-nitroimidazole and ethylene oxide. The steps include: 2-methyl-5-nitroimidazole Dissolve in a formic acid s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/92
Inventor 吕智国段小六程思远周拥军晏浩哲丁文波
Owner HUBEI HONGYUAN PHARMA
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