Method for synthesizing dichlofenac sodium

A technology of diclofenac sodium and a synthesis method, applied in the field of medicinal chemistry, can solve the problems of serious three-waste pollution and high labor protection requirements, and achieve the effects of environmental friendliness, good industrialization prospects and mild reaction conditions

Inactive Publication Date: 2005-02-16
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chen Fen'er et al. (Chinese Journal of Pharmaceutical Industry, 1998, 29, 339) carried out major improvements to this method, which was once a general method for domestic

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  • Method for synthesizing dichlofenac sodium
  • Method for synthesizing dichlofenac sodium
  • Method for synthesizing dichlofenac sodium

Examples

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example 1

[0023] Example 1 Cyclohexanone (50g, 0.51mol), cyclohexane (200mL) and triethyl phosphite (12g, 0.072mol) were placed in a dry reaction flask, and after heating and stirring to reflux, chlorine gas was slowly introduced until GLC showed a ring The hexanone starting material peaks all disappeared. When the content of II reaches 98%, stop flowing chlorine (consume about 185g of chlorine gas), and continue to stir and reflux for 40min. After the reaction was completed, it was cooled to 10°C, and a solid precipitated out, which was filtered. Wash with a small amount of cyclohexane and dry at 50°C to obtain white crystalline powder II (118g, 98%), mp 81-82°C.

example 2

[0024] Example 2 Cyclohexanone (50g, 0.51mol), petroleum ether (350mL) and triphenyl phosphite (1.58g, 0.0051mol) were placed in a dry reaction flask, and after heating and stirring to reflux, chlorine gas was slowly introduced until GLC showed a ring All peaks of the hexanone raw material disappeared, and when the content of compound (II) reached 98.5%, the introduction of chlorine gas was stopped, and stirring and reflux were continued for 30 min. After the reaction is complete, cool to 5-10°C, solid precipitates, and filter. Wash with a small amount of petroleum ether and dry at 50°C to obtain white crystalline powder II (111.9g, 94%), mp 79-81°C.

example 3

[0025] Example 3 Cyclohexanone (50g, 0.51mol), petroleum ether (350mL) and trimethyl phosphite (1.9g, 0.015mol) were placed in a dry reaction flask, and after heating and stirring to reflux, chlorine gas was slowly introduced until GLC showed a ring The peaks of the hexanone raw material all disappeared, and the chlorine gas was stopped, and the stirring and reflux were continued for 30 min. After the reaction was completed, it was cooled to 5°C, and a solid precipitated out, which was filtered. Wash with a small amount of petroleum ether and dry at 50°C to obtain white crystalline powder II (110.7g, 92%), mp 80-82°C.

[0026] Two, the preparation of o-nitrophenylacetic acid (III)

[0027]Example 1 Put o-nitrotoluene (41.2g, 0.30mol), sodium hydroxide (30g, 0.75mol), polyethylene glycol-600 (0.5g) and toluene (200mL) in a dry reaction flask, heat and stir to reflux for 1h , and then introduce carbon dioxide gas until no carbon dioxide is absorbed (about 6h, about 23.15g cons...

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Abstract

The invention provides a synthetic method of sodium diclofenac. The method includes the following steps: 1. Make the 2, 2, 6, 6-tetrachloride cyclohexanone (II) from the cyclohexanone through chlorination. 2. The carboxylation reaction occurs to the close nitrotoluene and carbon dioxide after the phase-transfer catalysis to get the close nitrophenyl acetic acid (III). 3. The hydrogenation reaction happens to the compound (III) catalysed by the polymer catalyst Pd/D-296 to produce the close aminophenyl acetic acid (IV). 4. The condensation reaction occurs to the compound IV and compound II to produce the compound of N-(2-carboxymerhy1 phenyl)-2,2,6,6-hexamethylene imine (V). 5. After the aromatization reaction and salifying happen to the compound V, we get the sodium diclofenac (I). By the close nitrotoluene, the yield is 85%. The invention is featured by facility of the raw material, simple operation, mild reation condition and easy industrialization.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a method for synthesizing diclofenac sodium, a non-steroidal anti-inflammatory analgesic. [0002] Background technique [0003] Diclofenac sodium (I) is a powerful third-generation non-steroidal anti-inflammatory antipyretic analgesic, widely used in chronic rheumatoid arthritis, deformed spondylosis, neuralgia, cold syndrome, pharyngitis, dysmenorrhea, surgery and after tooth extraction. Analgesic, anti-inflammatory, etc. Its anti-inflammatory strength rivals that of ibuprofen and naproxen. But the gastrointestinal reaction is much smaller than that of naproxen and ibuprofen. It has the characteristics of definite curative effect and mild side effects. [0004] British Patent 1132128, U.S. Patent 3558690 and Fei Shengqian etc. (Pharmaceutical Industry, 1979, 10, 14) have described that take o-chlorobenzoic acid as starting raw material and make key intermediate 2 through ...

Claims

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Application Information

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IPC IPC(8): C07C227/12C07C229/42
Inventor 陈芬儿戴惠芳陈旭翔匡云艳
Owner FUDAN UNIV
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