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Method for preparing diclofenac sodium

A technology of diclofenac and dichlorophenyl is applied in the field of preparation of diclofenac, can solve the problems of complicated operation, expensive raw materials, toxic raw materials and the like, and achieves the effects of simple operation, cheap raw materials, and easy availability of raw materials

Inactive Publication Date: 2013-06-12
中国人民解放军防化学院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In the above synthetic route, there are many steps, complicated operation, expensive raw materials, low yield and other shortcomings, and some synthetic routes also use toxic raw materials and other problems

Method used

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  • Method for preparing diclofenac sodium
  • Method for preparing diclofenac sodium

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preparation example Construction

[0024] The total reaction equation of the preparation method of diclofenac of the present invention is as follows:

[0025]

Embodiment 1

[0027] (a) the preparation of N-(2,6-dichlorophenyl) phenylacetamide (IV)

[0028] Add 16.20g (0.1mol) of 2,6-dichloroaniline and 9.49g (0.12mol) of pyridine to a 250ml three-necked flask equipped with a thermometer, a constant pressure dropping funnel, a reflux condenser and anhydrous calcium chloride drying tube. and 100ml acetone. After stirring, cooling in an ice-water bath, 15.45 g (0.1 mol) of phenylacetyl chloride was slowly added dropwise. After the addition was complete, the ice-water bath was removed. Heating, reflux 4h. Stop responding.

[0029] The reaction solution was poured into 250ml of 1.5mol / L hydrochloric acid solution while hot, and a large amount of yellow blocky solids appeared. The solid was filtered off and washed successively with 100ml×2 3mol / L hydrochloric acid solution, 100ml×2 1mol / L NaOH solution, and 100ml×2 deionized water. After drying, a yellow solid was obtained. 26.50 g of white needle-like crystals were obtained by recrystallization f...

Embodiment 2

[0039] (a) the preparation of N-(2,6-dichlorophenyl) phenylacetamide (IV)

[0040] Add 16.20g (0.1mol) of 2,6-dichloroaniline, 12.12g (0.12mol) of three Ethylamine and 150ml of dichloromethane. Stir and cool in an ice-water bath, slowly add 15.45 g (0.1 mol) of phenylacetyl chloride dropwise, and control the temperature of the reaction solution not to exceed 25°C. After the addition was complete, the ice-water bath was removed. Heating, reflux 6h. Stop responding.

[0041] After the reaction was completed, 50 ml of deionized water was added to the reaction solution, and a large amount of white solids were precipitated. Filter and wash the filter cake with 100ml×3 deionized water. The filtrate was separated and the organic phase was separated. The organic phase was washed successively with 50ml×2 10% NaOH solution, 50ml×2 3mol / L hydrochloric acid solution, and 250ml×2 deionized water. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was disti...

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Abstract

The invention discloses a method for preparing diclofenac sodium. The method is characterized by comprising the following steps of: obtaining N-chloro-N-(2,6-dichlorophenyl)phenylacetamide (III) through reacting a chloride reagent with N-(2,6-dichlorophenyl)phenylacetamide (IV); obtaining 1-(2,6-dichlorophenyl)-2-indolinone (II) through reacting N-chloro-N-(2,6-dichlorophenyl)phenylacetamide (III) with a certain amount of Lewis acid in an organic solvent; and finally obtaining diclofenac sodium (I) through enabling the 1-(2,6-dichlorophenyl)-2-indolinone (II) to be subjected to hydrolysis reaction in a sodium hydroxide solution. The method disclosed by the invention has the characteristics of simplicity in operation, easily-available reagents, low cost, mild conditions and the like, and provides a novel processing route for the synthesis of diclofenac sodium.

Description

technical field [0001] The invention belongs to the field of chemical drug synthesis, and more specifically relates to a preparation method of diclofenac. Background technique [0002] Diclofenac sodium (diclofenac sodium) is a third-generation non-steroidal powerful anti-inflammatory analgesic. It was listed in my country in the mid-1980s. Pain and fever caused by various reasons. Compared with other anti-inflammatory analgesics, its curative effect is stronger, 2-2.5 times stronger than indomethacin, 20-50 times stronger than aspirin; oral absorption is rapid, and the peak blood concentration can be reached within 2 hours; excretion is fast, long-term use without pain Accumulative effect; small individual differences, this product occupies a leading position in anti-rheumatic drugs. [0003] Regarding the chemical synthesis method of diclofenac, literature reports mainly contain the following 6 routes: [0004] 1), 2-(2,6-dichloroanilino) benzoyl chloride and diethyl mal...

Claims

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Application Information

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IPC IPC(8): C07C229/42C07C227/22
Inventor 田兴涛任丽君向玉联樊启平黄志平陈虹周蕾
Owner 中国人民解放军防化学院
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