Preparation method of furosemide

A technology of furosemide and furosemide, applied in directions such as organic chemistry, can solve the problems of high synthesis cost, high price, unfavorable industrialized production and the like, and achieve the effects of low cost, convenient operation, and easy availability of raw materials

Inactive Publication Date: 2016-08-31
HEZE CITY FANGMING PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But used raw material 4-chloro-2-fluoro-5-sulfamoylbenzoic acid is expensive, and the synthetic cost is higher, is unfavorable for industrialized production

Method used

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  • Preparation method of furosemide
  • Preparation method of furosemide

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Embodiment 1

[0016] Add 150ml of dimethyl sulfoxide into the reaction flask, then add 81g of 2,4-dichloro-5-sulfonylaminobenzoic acid and 30g of sodium bicarbonate, fill it with nitrogen for three times, and then raise the temperature to the reaction temperature of 130°C. Start to add 87g of furfurylamine dropwise, keep it warm for 6 hours, cool down to 30°C, adjust the pH to 3-4 with 10% hydrochloric acid, cool down to 20°C, keep for 2 hours, precipitate crystals, and filter out to obtain crude furosemide , Put the crude product into a three-necked flask, add 200ml of ethanol, 200ml of water, and 10g of sodium hydroxide, stir and heat up to 70°C to dissolve, then add 5g of activated carbon, filter it after 30 minutes, and cool the filtrate to room temperature, adjust the pH with 15% hydrochloric acid Value, solid precipitated, until PH = 3-4, kept for 2 hours, suction filtered, and the filter cake was dried to obtain 70.5g of furosemide, which was analyzed by HPLC with a purity of ≥99.0%. ...

Embodiment 2

[0018] Add 150ml of N,N-dimethylformamide into the reaction flask, then add 81g of 2,4-dichloro-5-sulfonylaminobenzoic acid and 30g of sodium bicarbonate, replace with nitrogen, and then heat up to the reaction flask At a temperature of 130°C, start to add 87g of furfurylamine dropwise. After dropping, keep it warm for 5 hours, cool down to 30°C, adjust the pH to 3-4 with 10% hydrochloric acid, cool down to 20°C, keep for 2 hours, precipitate crystals, and filter out to obtain For the crude product of furosemide, put the crude product into a three-necked flask, add 200ml of ethanol, 200ml of water, and 12g of sodium hydroxide, stir and heat up to 70°C to dissolve, add 5g of activated carbon, heat filter after 60 minutes, and cool the filtrate to room temperature. Adjust the PH value with % hydrochloric acid, and precipitate a solid until PH = 3-4, keep for 1 hour, filter with suction, and dry the filter cake to obtain 64.2 g of furosemide. After HPLC analysis, the purity is ≥99...

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Abstract

The invention belongs to the technical field of pharmacy and discloses a preparation method of furosemide. The preparation method comprises putting 2, 4-dichloro-5-sulfamoylbenzoic acid and an acid-binding agent into an appropriate solvent, heating the solution to a certain temperature in an inert gas protective atmosphere, dropwisely adding furfuryl amine into the solution, after the reaction, adjusting pH through an acid so that crystals are precipitated, filtering the crystals to obtain a furosemide crude product, refining the crude product through an organic solvent-water mixed solvent, adjusting pH to greater than 7, carrying out heating so that the crude product is dissolved, carrying out decoloration through activated carbon, carrying out hot filtration, adjusting pH of the filtrate through an acid so that solids are precipitated and carrying out filtration and drying to obtain furosemide. The preparation method utilizes cheap and easily available raw materials, has a high conversion rate, less side products and high product purity, has simple processes and is suitable for industrial production. A HPLC analysis result shows that purity is greater than or equal to 99.0% and a total yield is 71.2%.

Description

technical field [0001] The invention relates to a preparation method of furosemide, which belongs to the technical field of pharmacy. Background technique [0002] Furosemide, also known as furosemide, furosemide, diuretic, furosemide, diuretic acid, and abdominal acid. Chemical name: 2-(2-furylmethyl)amino-5-(sulfonylamino)-4-chlorobenzoic acid. Its structural formula is as follows (I): [0003] [0004] Furosemide can inhibit the reabsorption of Cl- and Na+ in the medullary and cortex of the ascending branch of the loop of Henle and play a diuretic effect. Its diuretic effect is rapid and powerful, and it is mostly used in severe cases where other diuretics are ineffective. Due to the obvious loss of water and electrolytes, it is not suitable for routine use. Drug poisoning can be used to accelerate the excretion of poison. Clinically, it is mainly used to treat peripheral edema caused by cardiac edema, renal edema, liver cirrhosis ascites, dysfunction or vascular ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/52
CPCC07D307/52
Inventor 朱文祥刘云霞
Owner HEZE CITY FANGMING PHARMA
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