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  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > December  >
In the Laboratory
The Microscale Laboratory
Keeping Your Students Awake: Facile Microscale Synthesis of Modafinil, a Modern Anti-Narcoleptic Drug
Evangelos Aktoudianakis, Rui Jun Lin, and Andrew P. Dicks
Department of Chemistry, University of Toronto, Ontario, Canada, M5S 3H6
Cover
December 2006
Vol. 83 No. 12
p. 1832

Abstract
This article describes the microscale preparation of modafinil, a pharmaceutical recently approved for the treatment of narcolepsy, by a sulfide oxidation reaction. The synthesis is straightforward and appropriate as part of a midlevel undergraduate organic laboratory. An unusual feature of modafinil is the presence of a chiral sulfoxide functionality where a sulfur atom acts as a stereocenter. This apprises students that atoms other than carbon can act as centers of chirality. The diastereotopic nature of protons adjacent to the sulfur stereocenter can be identified by 1H NMR spectroscopy, and functional group changes monitored by IR spectroscopy. The nature of modafinil and its role in society as an anti-narcoleptic is a source of attraction and fascination among undergraduates.
Supplement
Instructions for the students, notes for the instructor, synthesis of 2-(diphenylmethylthio)acetamide, and spectra are available.
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Citation
Aktoudianakis, Evangelos; Lin, Rui Jun; Dicks, Andrew P. J. Chem. Educ. 2006 83 1832.
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Keywords
Chirality / Optical Activity; Drugs / Pharmaceuticals; Hands-On Learning / Manipulatives; IR Spectroscopy; Laboratory Instruction; Mechanisms of Reactions; Microscale Lab; NMR Spectroscopy; Organic Chemistry; Second-Year Undergraduate; Stereochemistry; Synthesis
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History
Created:
Last Updated:
10/30/2006
11/7/2006
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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