Facile Amide Bond Formation with TCFH–NMI in an Organic Laboratory Course

• Oliver W. M. Baldwin ^[1] ; Linden H. Conrad-Marut ^[1] ; Gregory L. Beutner ^[2] ; David A. Vosburg ^[1]
  1. [1] Harvey Mudd College

     Harvey Mudd College

     Estados Unidos

     
  2. [2] Bristol Myers Squibb, United States
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 99, Nº 11, 2022, págs. 3747-3751
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • 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 (1H, 13C, 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.