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A kind of preparation method of secnidazole

A technology for secnidazole and nitroimidazole, which is applied in the field of preparation of secnidazole, can solve the problems of corrosion of equipment and pipelines, difficult preparation, complicated process, etc., and achieves reduction of waste water discharge and avoidance of the use of acid and alkali. , the effect of simplifying the production process

Active Publication Date: 2015-09-02
湖北金赛药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Although the yield of this method has been improved, dry hydrogen chloride gas will be used in the reaction process, which is not easy to prepare, and will cause great corrosion to equipment and pipelines. It also needs to adjust the pH value twice, and the process is complicated and It pollutes the environment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] In a 1000L reactor, put 550L ethyl acetate (moisture less than 0.5%) and 85Kg (0.67Kmol) 2-methyl-5-nitroimidazole, stir and cool down to below 5°C, slowly add 130Kg ( 0.977Kmol) of anhydrous aluminum chloride, after adding, stir for 1 hour, add 60Kg (1.03Kmol) of propylene oxide dropwise below 10°C, it takes about 4 hours to complete the dropwise addition, and keep the reaction at 10°C for 3 hours. Transfer to the recovery kettle, recover ethyl acetate under reduced pressure in a 50°C hot water bath, and recover about 400L (it can be used next time).

[0038] The reaction solution was pumped into the hydrolysis kettle, 500Kg of water was added, stirred for 1 hour, cooled to 10°C, and filtered with suction to obtain 10Kg of unreacted 2-methyl-5-imidazolium nitro. The filtrate was pumped into the extraction kettle, 200L of ethyl acetate was added, stirred for 30 minutes, and allowed to stand for 30 minutes. The organic layer was separated, and the aqueous layer was extr...

Embodiment 2

[0041] In a 1000L reactor, put 550L ethyl acetate (moisture less than 0.5%) and 85Kg (0.67Kmol) 2-methyl-5-nitroimidazole, stir and cool down to below 5°C, slowly add 133Kg ( 0.977Kmol) anhydrous zinc chloride, after adding, stir for 1 hour, add 68.5Kg (1.18Kmol) propylene oxide dropwise below 10°C, it takes about 4 hours to complete the dropwise addition, and keep warm at 10°C for 3 hours. Transfer to the recovery kettle, recover ethyl acetate under reduced pressure in a 50°C hot water bath, and recover about 400L (it can be used next time).

[0042] Pump the reaction solution into the hydrolysis tank, add 620Kg of mother liquor produced in the previous batch or previous batches, stir for 1 hour, cool down to 8°C, and filter with suction to obtain 10Kg of unreacted 2-methyl-5-imidazolium nitro. The filtrate was pumped into an extraction kettle, 200L of ethyl acetate was added, stirred for 30 minutes, allowed to stand for 30 minutes, the organic layer was separated, and extrac...

Embodiment 3

[0045] In a 1000L reactor, put 500L ethyl acetate (moisture less than 0.5%) and 85Kg (0.67Kmol) 2-methyl-5-nitroimidazole, stir and cool down to below 5°C, slowly add 125Kg ( 0.977Kmol) anhydrous aluminum chloride, after adding, stir for 1 hour, drop 60Kg (1.03Kmol) propylene oxide below 10°C, it takes about 4 hours to complete the dropwise addition, and keep warm at 10°C for 4 hours. Transfer to the recovery kettle, recover ethyl acetate under reduced pressure in a 50°C hot water bath, and recover about 360L (it can be used next time).

[0046] Pump the reaction solution into the hydrolysis tank, add 650Kg of mother liquor produced in the previous batch or previous batches, stir for 1 hour, cool down to 10°C, and filter with suction to obtain 10Kg of unreacted 2-methyl-5-imidazolium nitro. The filtrate was pumped into an extraction kettle, 200L of ethyl acetate was added, stirred for 30 minutes, allowed to stand for 30 minutes, the organic layer was separated, and the water l...

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PUM

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Abstract

The invention discloses a preparation method of secnidazole, belonging to the field of medicine chemical technology. The preparation method comprises the following steps: (1) in the presence of lewis acid, reacting 2-methyl-5-nitroimidazole with epoxy propane in an organic solvent, separating an aqueous secnidazole solution from a reaction product; (2) adding hydrolysate into the aqueous secnidazole solution; after hydrolysis is completed, performing cooling and solid-liquid separation to remove unreacted 2-methyl-5-nitroimidazole; carrying out extraction, concentration, crystallization and solid-liquid separation to obtain crude secnidazole and crude mother liquor, wherein the mass ratio of hydrolate to 2-methyl-5-nitroimidazole is 5.5-8.0:1; (3) dissolving the crude secnidazole into dichloromethane, and carrying out solid-liquid separation, distillation, decoloring, crystallization and solid-liquid separation to obtain refined secnidazole and refined mother liquid. The preparation method for secnidazole has the advantages of avoiding the use of acid and alkali, lowering the cost, simplifying the process and improving the yield.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to a preparation method of secnidazole. Background technique [0002] Secnidazole (1-(2-hydroxypropyl)-2-methyl-5-nitro-1H-imidazole hemihydrate) is a highly effective anti-amoeba and antigen biological drug, and its demand is growing rapidly. About the preparation method of secnidazole, currently reported roughly contains following several kinds: [0003] 1. The synthesis of secnidazole was initially reported by Rhone-poulec S.A (refer to French patent 1427627 (application date: October 10, 1963) and French patent M3270 (application date: December 30, 1963)); 2-Methyl-5-nitro-imidazole (1 mol) was dissolved in a large amount of formic acid (85%) (7.88 parts). To the above solution cooled to -14°C was added a large amount of propylene oxide (5 mol) over 1.5 hours. The mixture was left overnight and excess formic acid was removed in vacuo. Water...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/94
CPCC07D233/94
Inventor 熊开文赵继舒
Owner 湖北金赛药业有限公司
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