KMID : 1059520180620030187
|
|
Journal of the Korean Chemical Society 2018 Volume.62 No. 3 p.187 ~ p.190
|
|
Laboratory Experiment: Synthesis and Characterization of 4-Methyl-N-(phenylacetyl)benzenesulfonamide through Cu(I)-Catalysis
|
|
Jung Byung-Hyuck
|
|
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, 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.
|
|
KEYWORD
|
|
Inquiry-based/discovery learning, Spectroscopy, Alkynes, Amides, Catalysis
|
|
FullTexts / Linksout information
|
|
|
|
Listed journal information
|
|
|
|