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Method for synthesizing 5-difluoromethoxy-2-mercapto-1H-benzimidazole

A technology of difluoromethoxy o-phenylenediamine and difluoromethoxy, applied in the field of synthesis of 5-difluoromethoxy-2-mercapto-1H-benzimidazole, can solve the problem of single reaction temperature, organic There are many solvents and high cost, etc., to achieve the effect of simple process operation, mild reaction conditions and low cost

Active Publication Date: 2014-01-29
JIANGSU YUXIANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this step condensation and ring closure reaction, the reaction temperature is relatively single, only one reaction stage, and the yield is low
Therefore, there are various defects in various existing synthetic methods, or the yield is low, or there are too many organic solvents, resulting in relatively expensive costs.
The existing technical routes need to be improved in terms of environmental friendliness and cost

Method used

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  • Method for synthesizing 5-difluoromethoxy-2-mercapto-1H-benzimidazole
  • Method for synthesizing 5-difluoromethoxy-2-mercapto-1H-benzimidazole
  • Method for synthesizing 5-difluoromethoxy-2-mercapto-1H-benzimidazole

Examples

Experimental program
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Effect test

Embodiment 1

[0038] In a four-neck flask equipped with mechanical stirring, reflux condenser, and thermometer, mix lye: 6.6 grams of sodium carbonate + 20 grams of tap water, stir until completely dissolved, slightly lower the temperature, and add 4-difluoromethoxy o-phenylenediamine 34.8 g, stirred for 20 min. Raise the temperature to 30°C, add 20 grams of carbon disulfide dropwise at 25-35°C, keep warm and condense at 30-40°C for 6 hours, continue to heat up to 60-70°C and keep warm for 6 hours, after the ring closure is complete, add activated carbon for decolorization, and adjust the pH of the filtrate with sulfuric acid to 5-6, filtered, washed, and dried to obtain 33.2 grams of 5-difluoromethoxy-2-mercapto-1H-benzimidazole, based on 4-difluoromethoxy o-phenylenediamine, the yield was 95.4 %.

Embodiment 2

[0040] In a four-necked flask equipped with a mechanical stirrer, a reflux condenser, and a thermometer, mix lye: 5.5 grams of sodium hydroxide + 25 grams of tap water, stir until completely dissolved, cool down slightly, and add 4-difluoromethoxy phthalate 34.8 g of amine, stirred for 20 min. Raise the temperature to 40°C, add 28 grams of carbon disulfide dropwise at 35-45°C, keep warm and condense at 40-45°C for 3 hours after dropping, continue to heat up to 80-90°C and keep warm for 1 hour, after the ring closure is complete, add activated carbon for decolorization, and adjust the pH of the filtrate with hydrochloric acid to 5. Filter, wash, and dry to obtain 37.4 g of 5-difluoromethoxy-2-mercapto-1H-benzimidazole, with a yield of 107.5% based on 4-difluoromethoxy-o-phenylenediamine.

Embodiment 3

[0042]In a four-necked flask equipped with mechanical stirring, a reflux condenser, and a thermometer, prepare lye: 13.0 grams of potassium hydroxide + 30 grams of tap water, stir until completely dissolved, slightly lower the temperature, and add 4-difluoromethoxy phthalate 34.8 g of amine, stirred for 20 min. Raise the temperature to 40°C, add 28 grams of carbon disulfide dropwise at 35-45°C, keep warm and condense at 40-45°C for 3 hours after dropping, continue to heat up to 80-90°C and keep warm for 3 hours, after the ring closure is complete, add activated carbon for decolorization, and adjust the pH of the filtrate with phosphoric acid to 5. Filter, wash, and dry to obtain 37.8 g of 5-difluoromethoxy-2-mercapto-1H-benzimidazole, with a yield of 108.6% based on 4-difluoromethoxy-o-phenylenediamine.

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Abstract

The invention relates to a method for synthesizing 5-difluoromethoxy-2-mercapto-1H-benzimidazole. According to the method, the target product 5-difluoromethoxy-2-mercapto-1H-benzimidazole is prepared through reacting 4-difluoromethoxy-o-phenylenediamine, which serves as a main starting material, with alkali and carbon disulfide in a water solvent and controlling the process conditions of two stages, namely a condensation reaction stage and a cyclization reaction stage. In two-step reaction steps, a single reaction solvent, namely water, is adopted, and any organic solvent is not adopted. By using the method disclosed by the invention, the reaction conditions are mild, the process operations are simple and environmental-friendly, the cost is low, and the yield is high.

Description

Technical field [0001] The invention relates to a synthesis method of 5-difluoromethoxy-2-mercapto-1H-benzimidazole. Background technique [0002] 5-Difluoromethoxy-2-mercapto-1H-benzimidazole is an important intermediate of pantoprazole. Its CAS number is [97963-62-7] and its molecular formula is as follows. [0003] [0004] Pantoprazole is a proton pump inhibitor drug developed by the German company Byk Gulden. It mainly treats duodenal and gastric ulcers and relieves severe reflux esophagitis. Pantoprazole is another important proton pump inhibitor after omeprazole and lansoprazole, and is used to treat gastric diseases related to Helicobacter pylori. Pantoprazole is its trade name, and its chemical name is: 5-difluoromethoxy-2-[(3,4-dimethoxy-2-piperidyl)-methyl]-sulfinyl -1 Hydro-benzimidazole. The molecular structure formula is as follows: [0005] [0006] 5-Difluoromethoxy-2-mercapto-1H-benzimidazole is an important intermediate of pantoprazole. According...

Claims

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Application Information

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IPC IPC(8): C07D235/28
CPCC07D235/28
Inventor 张治国程云涛钟旭辉李清龙程红伟
Owner JIANGSU YUXIANG CHEM
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