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http://dx.doi.org/10.5012/jkcs.2018.62.3.187

Laboratory Experiment: Synthesis and Characterization of 4-Methyl-N-(phenylacetyl)benzenesulfonamide through Cu(I)-Catalysis  

Jung, Byunghyuck (School of Basic Science, DGIST)
Publication Information
Journal of the Korean Chemical Society / v.62, no.3, 2018 , pp. 187-190 More about this Journal
Abstract
A three-component coupling reaction of phenylacetylene, p-toluenesulfonyl azide, and water through copper catalysis is described to provide knowledge of spectroscopy and catalytic reactions and to introduce current research topics in organic chemistry for second-year undergraduate students. In the presence of stoichiometric amounts of phenylacetylene, p-toluenesulfonyl azide, and triethylamine, the reaction was performed with 4 mol% CuCl in water as the sole solvent and was completed in 1.5 h. A practical purification method and recrystallization of the crude reaction mixture resulted in the rapid isolation of the desired product with yields of 42~65%. Students characterized 4-methyl-N-(phenylacetyl)benzenesulfonamide by using melting-point determination, infrared spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy. This experimental procedure and spectroscopic data analysis will serve as a platform for students to apply classroom knowledge in practical state-of-the-art research.
Keywords
Inquiry-based/discovery learning; Spectroscopy; Alkynes; Amides; Catalysis;
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