Preparation method of aceclofenac

A technology of butaclofenac and an operating method, applied in the fields of microwave reaction and chemical pharmacy, can solve the problems of uneven heating, slow heating process and the like, and achieve the effects of less diclofenac content, easy purification and high conversion rate

Active Publication Date: 2019-08-20
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional heating method is to heat the substance from the outside to the inside through conduction,

Method used

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  • Preparation method of aceclofenac
  • Preparation method of aceclofenac
  • Preparation method of aceclofenac

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation of 2-((2,6-dichlorophenyl)amino)phenylacetoxyacetic acid tert-butyl ester (aceclofenac tert-butyl ester)

[0032]

[0033] Diclofenac sodium (10 g, 33.8 mmol), tert-butyl bromoacetate (7.85 g, 40.3 mmol), KI (0.26 g, 1.6 mmol), acetonitrile (30 mL) were added to a 100 mL flask. Microwave conditions were set, the power was 100W, the temperature was 30°C, and the reaction time was 15min. After the reaction was completed, the reaction solution was poured into 100 mL of purified water and stirred for 2 h for crystallization. After suction filtration, the filter cake was washed twice with 100 mL of purified water to obtain a crude product of aceclofenac tert-butyl ester.

[0034] The crude product and ethanol (280 mL) were added to a 500 mL three-necked flask, heated to 75°C, until the solid was completely dissolved, stirred and cooled to 10°C for crystallization for 2 h, suction filtered, and the filter cake was washed twice with 100 mL of ethanol...

Embodiment 2

[0035] Example 2: Preparation of Aceclofenac

[0036]

[0037] Aceclofenac tert-butyl ester (7.0 g, 17.1 mmol), formic acid (14 mL, 371.3 mmol) and acetone (3.5 mL) were added to a 50 mL three-necked flask. Microwave conditions were set, the power was 200W, the temperature was 65°C, and the reaction time was 10min. After the reaction was completed, the reaction solution was slowly poured into 80 mL of purified water, stirred for 10 minutes, filtered with suction, and the filter cake was washed twice with 20 mL of purified water to obtain a crude product. The crude product was dissolved in toluene (12 mL), and the temperature was raised to 90 °C. After the solid was completely dissolved, the temperature was stirred and cooled to 10 °C for crystallization, and the crystals were grown for 2 h. g, the yield is 96.3%.

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Abstract

The invention discloses a microwave-assisted preparation method of aceclofenac. The method is as follows: under the microwave condition, a compound 2 and a compound 3 are reacted to form a compound 4under the catalysis of KI; and under the microwave condition, a reaction of the compound 4 is carried out in a mixed solvent of formic acid and acetone. According to the method, the acidolysis of aceclofenac tert-butyl ester is carried out in the mixture of formic acid and acetone under the microwave condition, the acidolysis method has high selectivity, the fracture of the ethoxyl group in aceclofenac tert-butyl ester is reduced to the lowest limit, the conversion rate of the acidolysis reaction is high, the diclofenac content in the product is extremely small, the product is easy to refine,and the purity is high.

Description

[0001] (1) Technical field [0002] The invention relates to a preparation method of an anti-inflammatory and analgesic drug, in particular to a preparation method of aceclofenac under the assistance of microwaves, belonging to the fields of chemical pharmacy and microwave reaction. [0003] (2) Background technology [0004] Aceclofenac, chemical name is 2-((2,6-dichlorophenyl)amino)phenylacetoxyacetic acid, English name: Aceclofenac, structural formula is: [0005] [0006] In the traditional aceclofenac synthesis reaction, the heat conduction heating method is adopted, which is usually heated to a higher temperature, and the energy consumption is large, and the traditional reaction reaction time is long, and there are many impurities generated during the acidolysis process, and the post-processing is difficult. [0007] CN2007192213 discloses a preparation method of aceclofenac, using diclofenac sodium and tert-butyl chloroacetate, under the action of triethylamine, heati...

Claims

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Application Information

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IPC IPC(8): C07C227/18C07C229/42
CPCC07C227/18C07C229/42
Inventor 王建伟熊加赵单伟光
Owner ZHEJIANG UNIV OF TECH
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