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

대한화학회지 2018년 62권 3호 p.187 ~ 190
 ( Jung Byung-Hyuck ) - DGIST School of Basic Science


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, ptoluenesulfonyl 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.


Inquiry-based/discovery learning; Spectroscopy; Alkynes; Amides; Catalysis
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