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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 Keywords
- Inquiry-based/discovery learning; Spectroscopy; Alkynes; Amides; Catalysis
- Keywords
- H BOND ACTIVATION; AMIDE SYNTHESIS; WATER; CATALYST; CLICK
- 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
-
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Jung, Byunghyuck
Asymmetric Organic Synthesis and Drug Synthesis Laboratory
-
Research Interests
Organic Synthesis; Organo-transition metal chemistry; Catalytic Asymmetric Synthesis; Synthetic Methodologies; Synthesis of Natural Products and Drugs
- Files:
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- Collection:
- Department of Physics and ChemistryAsymmetric Organic Synthesis and Drug Synthesis Laboratory1. Journal Articles
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