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Synthesis of celecoxib in the undergraduate organic chemistry or medicinal chemistry laboratories; conventional vs. microwave heating
Anderluh, Marko
A method for a two-step synthesis of celecoxib in the undergraduate organic chemistry or medicinal chemistry laboratories is reported. The experiment requires two 3.5 hour lab periods and the ...standard equipment for organic/medicinal chemistry course, plus a monomode microwave reactor. In the first session, students condense 4-methylacetophenone and ethyl trifluoroacetate to yield 4,4,4-trifluoro-1-(p-tolyl)butan-1,3-dione. The latter is then condensed in a second session with 4-hydrazinobenzene-1-sulfonamide hydrochloride to yield corresponding 1,5-arylpyrazole (celecoxib) using either conventional heating or microwave-assisted synthesis. Both procedures give a crystalline product with a reasonably high yield that is easy to isolate and purify, and both procedures are robust and practical. The 1H-NMR spectra of both intermediate and final product are easily interpreted by the students. The comparison of both procedures used for the same reaction offers an excellent basis to demonstrate the advantages of the microwave-assisted over conventional heating.
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