ChemicalBook CAS DataBase List Celecoxib

Celecoxib synthesis

5synthesis methods

Product Name:Celecoxib
CAS Number:169590-42-5
Molecular formula:C17H14F3N3O2S
Molecular Weight:381.37

Celecoxib is prepared by condensation of 4-methylacetophenone with ethyl trifluoroacetate to give 4,4,4-trifluoro-1-(4- methylphenyl)butane-1,3-dione, which is cyclized with 4-hydrazinophenylsulfonamide.

Benzenesulfonamide, 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-N,N-bis(phenylmethyl)-

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Yield:169590-42-5 99%

Reaction Conditions:

with sulfuric acid at 20; for 8 h;

Steps:

General procedure: To a 5mL round bottom flask were added 4c or 4d(0.1mmol), concentrated H₂SO₄ (1mL). The reaction was stirred at room temperature for 8h, and then was added to water (10mL) carefully. The mixture was extracted with Et₂O. The organic layer was dried over Na₂SO₄, filtered, and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM/EtOAc=10/1) to afford Celecoxib or Mavacoxib (99% yield) as a white solid. The analytical data are in accordance with literature.^9,16,17

References:

Wang, Yongdong;Han, Jing;Chen, Jie;Cao, Weiguo [Tetrahedron,2015,vol. 71,# 43,p. 8256 - 8262]