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Synthesis of celecoxib in the undergraduate organic chemistry or medicinal chemistry laboratories; conventional vs. microwave heating
Anderluh, Marko (Avtor)

URLURL - Predstavitvena datoteka, za dostop obiščite http://chemeducator.org/bibs/0018001/18100155.html Povezava se odpre v novem oknu

Izvleček
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.

Jezik:Angleški jezik
Ključne besede:organska kemija, medicinska kemija, aldehidi, laboratoriji, mikrovalovne pečice
Vrsta gradiva:Delo ni kategorizirano (r6)
Tipologija:1.01 - Izvirni znanstveni članek
Organizacija:FFA - Fakulteta za farmacijo
Leto izida:2013
Št. strani:str. 155-158
Številčenje:Vol. 18
UDK:547+615.4
ISSN pri članku:1430-4171
DOI:10.1007/s00897132496 Povezava se odpre v novem oknu
COBISS.SI-ID:3499377 Povezava se odpre v novem oknu
Število ogledov:1026
Število prenosov:207
Metapodatki:XML RDF-CHPDL DC-XML DC-RDF
 
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Naslov:#The #chemical educator
Skrajšan naslov:Chem. educator
Založnik:Boise State University
ISSN:1430-4171
COBISS.SI-ID:3499121 Povezava se odpre v novem oknu

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