Jump to main content
Jump to site search

Issue 1, 2021
Previous Article Next Article

Improved batch and flow syntheses of the nonsteroidal anti-inflammatory COX-2 inhibitor celecoxib

Author affiliations

Abstract

The comparison of an improved conventional batch mode synthesis of the nonsteroidal anti-inflammatory COX-2 inhibitor celecoxib with its flow chemistry alternative is reported. The stepwise and continuous flow synthesis of celecoxib was achieved by means of a Claisen condensation to access 4,4,4-trifluoro-1-(4-methyl-phenyl)-butane-1,3-dione followed by a cyclo-condensation reaction with 4-sulfamidophenylhydrazine hydrochloride to obtain the pyrazole moiety. A batch process was developed with improved work-up and purification (90% yield). This was successfully translated to flow in yields of 90–96% with greatly shortened reaction times (20 h vs. 1 h) and reduced chemical exposure.

Graphical abstract: Improved batch and flow syntheses of the nonsteroidal anti-inflammatory COX-2 inhibitor celecoxib

Back to tab navigation

Supplementary files

Article information


Submitted
01 Sep 2020
Accepted
20 Oct 2020
First published
20 Oct 2020

React. Chem. Eng., 2021,6, 138-146
Article type
Paper

Improved batch and flow syntheses of the nonsteroidal anti-inflammatory COX-2 inhibitor celecoxib

C. Scholtz and D. L. Riley, React. Chem. Eng., 2021, 6, 138
DOI: 10.1039/D0RE00346H

Social activity

Search articles by author

Spotlight

Advertisements