NotesFAQContact Us
Collection
Advanced
Search Tips
Back to results
Peer reviewed Peer reviewed
Direct linkDirect link
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.]
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