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Laboratory experiment: Synthesis and characterization of 4-methyl-N-(phenylacetyl)benzenesulfonamide through Cu(I)-catalysis

Title
Laboratory experiment: Synthesis and characterization of 4-methyl-N-(phenylacetyl)benzenesulfonamide through Cu(I)-catalysis
Authors
Jung, Byunghyuck
DGIST Authors
Jung, Byunghyuck
Issue Date
2018-06
Citation
Journal of the Korean Chemical Society, 62(3), 187-190
Type
Article
Article Type
Article
Author Keyword
Alkynes; Amides; Catalysis; Inquiry-based/discovery learning; Spectroscopy
ISSN
1017-2548
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. © Korean Chemical Society. All Rights Reserved.
URI
http://hdl.handle.net/20.500.11750/6648
DOI
10.5012/jkcs.2018.62.3.187
Publisher
Korean Chemical Society
Related Researcher
  • Author Jung, Byunghyuck  
  • Research Interests Organic Synthesis; Organo-transition metal chemistry
Files:
There are no files associated with this item.
Collection:
School of Undergraduate Studies1. Journal Articles


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