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Method for preparing bumetanide

A technology of phenoxy and sulfonamido benzoic acid is applied in the preparation of sulfonic acid amides, medical preparations containing active ingredients, pharmaceutical formulations, etc., and can solve the problems of long reaction time, cumbersome post-processing, unsuitable for industrialized production and the like, Achieve the effect of low equipment requirements and simple operation

Inactive Publication Date: 2009-12-02
SUZHOU LIXIN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This process route needs to be carried out in complex dehydration reaction equipment, the reaction time is long, the post-treatment is cumbersome, and the yield of the obtained product is only about 40%, which is not suitable for industrial production

Method used

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  • Method for preparing bumetanide
  • Method for preparing bumetanide

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Combine 60g 3-amino-4-tolyloxy-5-sulfonamidobenzoic acid, 22ml n-butyraldehyde, 42ml boron trifluoride ether (containing about 47% boron trifluoride), 600ml methanol and 10g 5% palladium on carbon Add to a 1000ml autoclave and replace it with nitrogen and hydrogen three times respectively, so that the materials in the kettle will react at a temperature of 20℃~25℃ and a hydrogenation pressure of 1~2atm. After about 14h, the pressure in the reactor will not change. Indicates the end of hydrogen absorption. Discharge, filter and recover palladium-carbon. After adding 6g activated carbon to decolorize the filtrate for 10 minutes, filter, keep the filtrate, add the filtrate dropwise to 2400ml of water, precipitate solids, filter, wash the filter cake with water, and drain to obtain 66g of white solids. Bumetanide. The yield was 93%.

Embodiment 2

[0024] Add 60g 3-amino-4-tolyloxy-5-sulfonamidobenzoic acid, 22ml n-butyraldehyde, 42ml boron trichloride ether, 600ml ethanol and 10g 5% palladium charcoal into a 1000ml autoclave and use Replace with nitrogen and hydrogen three times, at a temperature of 20°C to 25°C and a pressure of 1 to 2 atm until the end of hydrogen absorption, about 14 hours. After the reaction is complete, the material is discharged and the palladium-carbon is recovered by filtration. The filtrate is added with 6g of activated carbon and refluxed for 10 minutes, and then filtered. The obtained filtrate is added dropwise to 2400ml of water to precipitate solids, filtered, the filter cake is washed with water and drained to obtain 64g of white solids, which is cloth Metanide, the yield is 90%.

Embodiment 3

[0026] Add 60g 3-amino-4-tolyloxy-5-sulfonamidobenzoic acid, 22ml n-butyraldehyde, 42ml boron trifluoride ether, 600ml methanol and 10g 10% palladium charcoal into a 1000ml autoclave and use Replace with nitrogen and hydrogen three times, at a temperature of 20°C to 25°C and a pressure of 1 to 2 atm until the end of hydrogen absorption, about 6 hours. After the reaction is completed, the reactants are filtered to recover the palladium-carbon. The reaction solution is added with 6g activated carbon and refluxed for 10 minutes, and then filtered. The resulting filtrate is added dropwise to 2400ml of water to separate out solids. Filter, wash the filter cake with water and drain to obtain 68g of white solids It is bumetanide with a yield of 96%.

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Abstract

The invention relates to a method for preparing bumetanide, which comprises that: 3-amino-4-phenoxy-5-sulfonylaminobenzoic acid and n-butanal are used as raw materials; firstly, the raw materials are subjected to condensation-dehydration reaction in the presence of a boron trihalide ether catalyst to generate 3-butylimine-4-phenoxy-5-sulfonylaminobenzoic acid; and then, the 3-butylimine-4-phenoxy-5-sulfonylaminobenzoic acid is catalyzed by palladium carbon and hydrogenated to form the bumetanide. The method has the advantages of simple operation, short reaction time and low equipment requirement, and is suitable for industrialized production; and the yield of a target product can reach more than 90 percent.

Description

Technical field [0001] The invention relates to a preparation method of bumetanide. Background technique [0002] Bumetanide (the chemical name is 3-n-butylamino-4-phenoxy-5-sulfonylaminobenzoic acid) is a potent medulla diuretic with a diuretic effect 40-60 times that of furosemide Above, it is mainly used to treat various cardiogenic, hepatitis B, renal and nutritional edema. [0003] In the prior art, bumetanide is mainly prepared through the following collectively called routes: [0004] [0005] This process route needs to be carried out in complex dehydration reaction equipment, the reaction time is long, the post-treatment is complicated, and the product yield is only about 40%, which is not suitable for industrial production. Summary of the invention [0006] The technical problem to be solved by the present invention is to overcome the shortcomings of the prior art and provide a method for preparing bumetanide, which has short reaction time, simple operation and high ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/39C07C303/40A61K31/63A61P7/10
CPCY02P20/582
Inventor 舒亮张爱青包志坚
Owner SUZHOU LIXIN PHARMA
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