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  Home > JCE Print > Journal of Chemical Education > Issues > 2003  > December  >
In the Laboratory
The Microscale Laboratory
Microscale Synthesis and Spectroscopic Analysis of Flutamide, an Antiandrogen Prostate Cancer Drug
Ryan G. Stabile and Andrew P. Dicks
Department of Chemistry, University of Toronto, Toronto, Ontario, Canada, M5S 3H6
Cover
December 2003
Vol. 80 No. 12
p. 1439
Abstract
The microscale preparation of flutamide, a nonsteroidal antiandrogen prescribed as Eulexin for the treatment of prostate cancer is outlined. The synthesis involves N-acylation of a trisubstituted aromatic compound, 3-trifluoromethyl-4-nitroaniline. The procedure is easily adapted to generate structural analogues of flutamide. A significant feature is the curricular flexibility afforded by this experiment. The fundamental reaction is appropriate within an introductory organic laboratory course, demonstrating amine and acid–halide reactivity. Functional group transformations can be observed by IR spectroscopy. 1H NMR spectra of reactant and products facilitate a thorough examination of shielding and deshielding effects and aromatic proton coupling. With more advanced students there exists the potential to discuss principles of retrosynthetic analysis, pharmaceutical synthesis, and structure–activity relationships.

See Featured Molecules.
Supplement
Instructions for the students, a prelaboratory assignment, notes for the instructor, and spectroscopic information are available.
*  Contents JCE2003p1439W.doc (Microsoft Word)
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More Information
*  Citation
 Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2003 80 1439.
*  Keywords
 Drugs / Pharmaceuticals; IR Spectroscopy; Laboratory Instruction; Mechanisms; Microscale; NMR Spectrometry; Organic Chemistry; Organic Synthesis
*  History
 Created:
Last Updated:		 October 31, 2003
February 28, 2005
Link to Featured Molecules added (April 2004).
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