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

다국어 초록 (Multilingual 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.

참고문헌 (Reference)

1 Allen, S. E., 113 : 6234-, 2013

2 Labinger, J. A., 417 : 507-, 2002

3 Davies, H. M. L., 40 : 1855-, 2011

4 Cho, S. H., 127 : 16046-, 2005

5 Yoo, E. J., 8 : 1347-, 2006

6 Cho, S. H., 46 : 1897-, 2007

7 McKee, J. R., 59 : 695-, 1982

8 Kono, H., 53 : 77-, 1973

9 Hansen, T. V., 82 : 1833-, 2005

10 Petrone, D. A., 116 : 8003-, 2016

11 Souillart, L., 115 : 9410-, 2015

12 Wencel-Delord, J., 40 : 4740-, 2011

13 Giri, R., 38 : 3242-, 2009

14 Schwarz, C. V., 46 : 632-, 2009

15 Nakamura, E., 10 : 158-, 2011

16 Guo, X. X., 115 : 1622-, 2015

17 McCann, S. D., 48 : 1756-, 2015

18 Glinski, M., 93 : 1623-, 2016

19 Lipshutz, B. H., 90 : 1514-, 2013

20 Ison, E. A., 89 : 1575-, 2012

21 Mendes, D. E., 88 : 1582-, 2011

22 Hegedus, L. S., "Transition Metals in the Synthesis of Complex Organic Molecules" University Science Books 1-, 2010

23 Crabtree, R. H., "The Organometallic Chemistry of the Transition Metals" John Wiley & Sons 1-, 2009

24 Osborne, J., "Science Education in Europe" 2008

25 Spessard, G. O., "Organometallic Chemistry" Oxford University Press 1-, 2010

26 "Nobel Prizes and Laureates in Chemistry"

27 Williamson, K. L., "Macroscale and Microscale Organic Experiments" Cengage Learning 490-, 2011

28 Williamson, K. L., "Macroscale and Microscale Organic Experiments" Cengage Learning 617-, 2010

29 "E-Eros Encyclopedia of Reagents for Organic Synthesis"

30 American Association for the Advancement of Science (AAAS), "Benchmarks for Science Literacy" Oxford University Press 1993