95455-39-3Relevant articles and documents
Interaction α-aminoamide - compose carbonyle. Mecanisme de formation des imidazolidinones-4
Pascal, R.,Lasperas, M.,Taillades, J.,Commeyras, A.,Perez-Rubalcaba, A.
, p. 329 - 337 (2007/10/02)
The reaction of α-N-methylaminopropionamide 1 with formaldehyde was studied in unbuffered aqueous solution.The reaction led to 1,5-dimethyl-4 imidazolidinone, 2a, in equilibrium with 3-hydroxymethyl 1,5-dimethyl 4-imidazolidinone, 3a, formed by addition of a second formaldehyde molecule.A kinetic study of the formation of 2a and 3a indicated that the addition of the amino group of 1 was a complete equilibrium.The reaction pathway involved the rate determining attack of the amide group of 1 on formaldehyde to form a hydroxymethyl amide intermediate, which was not isolated.The intramolecular assistance by the amino group, noted for this step, was interpreted as an attack of 1 in a zwitterionic form.Secondary amines catalyzed the formation of 2a and 3a by a pathway which involved the intermediate formation of iminium ions >N=CH2(1+).