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

Journal of the Korean Chemical Society

article

Byunghyuck Jung 

[1] School of Basic Science, DGIST

关键词: nquiry-based/discovery learning;    Spectroscopy;    Alkynes;    Amides;    Catalysis;   

DOI  :  10.5012/jkcs.2018.62.3.187

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

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.

【 授权许可】

Unknown