Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for synthesizing dichlofenac sodium

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

Inactive Publication Date: 2006-02-22
FUDAN UNIV
View PDF6 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 production (I), but the three wastes of this method are seriously polluted, labor protection requirements are high, and the total recovery rate is large Amplitude increase

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing dichlofenac sodium
  • Method for synthesizing dichlofenac sodium
  • Method for synthesizing dichlofenac sodium

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0023] Example 1 Cyclohexanone (50g, 0.51mol), cyclohexane (200mL) and triethyl phosphite (12g, 0.072mol) were placed in a dry reaction flask, heated and stirred to reflux, and 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 Put cyclohexanone (50g, 0.51mol), petroleum ether (350mL) and triphenyl phosphite (1.58g, 0.0051mol) in a dry reaction flask, heat and stir to reflux, then slowly introduce chlorine gas until GLC shows 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 Put cyclohexanone (50g, 0.51mol), petroleum ether (350mL) and trimethyl phosphite (1.9g, 0.015mol) in a dry reaction flask, heat and stir to reflux, then slowly introduce chlorine gas until GLC shows 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 consumed). After the reaction...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/42C07C227/04C07C227/12
Inventor 陈芬儿戴惠芳陈旭翔匡云艳
Owner FUDAN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com