Department of Chemistry
College of Letters & Science

Experiment 16: Biginelli Synthesis of a Heterocycle

Overview of the Biginelli Reaction

Due Dates:

Thursday, July 21 A/B

 

Chemical Safety Information:

Reagents and Solvents
Urea Ethyl aceteoacetate Hydrochloric acid
Benzaldehyde 4-Methoxybenzaldehyde 4-Nitrobenzaldehyde
3-Nitrobenzaldehyde Ethanol Sodium bicarbonate
Deuterated chloroform

 

Recommended Reading:

Loudon Section 19.11 Reactions of Aldehydes and Ketones with Amines

Organic Chemistry Portal, Overview of MultiComponent Reactions (MCRs), http://www.organic-chemistry.org/topics/multicomponent-reactions.shtm

Kappe, C. O. A Reexamination of the Mechanism of the Biginelli Dihydropyrimidine Synthesis. Support for an N-Acyliminium Ion Intermediate. J. Org. Chem. 1997, 62 (21), 7201–7204.

 

Experimental Spectra:

Biginelli 1H-NMR 14-Jul-2016

Sample 1H-NMR Spectra for All Products (not available for submission for credit)

 

Urea 1H-NMR FID (FOR REFERENCE ONLY)

4-methoxybenzaldehyde 1H-NMR FID (FOR REFERENCE ONLY)

Stock FID 1H-NMR for product from benzaldehyde (available for submission for credit, see laboratory manual for details)

Stock FID 1H-NMR for product from 4-methoxybenzaldehyde (available for submission for credit, see laboratory manual for details)

Stock FID 1H-NMR for product from 4-nitrobenzaldehyde (available for submission for credit, see laboratory manual for details)