ERIC Number: EJ1442866
Record Type: Journal
Publication Date: 2022-Nov
Pages: 5
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: EISSN-1938-1328
Facile Amide Bond Formation with TCFH-NMI in an Organic Laboratory Course
Oliver W. M. Baldwin; Linden H. Conrad-Marut; Gregory L. Beutner; David A. Vosburg
Journal of Chemical Education, v99 n11 p3747-3751 2022
A new undergraduate organic laboratory experiment has been developed for amide bond formation between biorenewable 2-furoic acid and either of two substituted piperazines to prepare medicinally relevant amide products using a procedure with industrial significance. The reactions proceeded smoothly under ambient conditions using the combination of N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate (TCFH) and N-methylimidazole (NMI) in a minimal volume of acetonitrile with a direct crystallization upon addition of water. Students successfully collected their product by filtration and then characterized it by NMR ([superscript 1]H, [superscript 13]C, COSY, DEPT-135, HSQC), IR, MS, and melting point. Students also explored the reaction mechanism and compared green chemistry aspects of their procedure with literature routes. A virtual version of the experiment was adapted for remote instruction. [This paper was presented at the Spring 2022 American Chemical Society National Meeting and the 2022 National Organic Symposium.]
Descriptors: Undergraduate Study, Organic Chemistry, Science Laboratories, Laboratory Experiments, Science Experiments, Scientific Concepts, Concept Formation, Distance Education, College Science
Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: National Science Foundation (NSF), Division of Chemistry (CHE)
Authoring Institution: N/A
Grant or Contract Numbers: 1725142