REACTION OF CYANOGUANIDINE WITH FORMALDEHYDE. I. HYDROXYMETHYLATION AND METHOXYMETHYLATION OF CYANOGUANIDINE.

Article abstract of DOI:10.1246/bcsj.56.3319

In order to examine the reactivity of cyanoguanidine (CG) with formaldehyde, CG was first hydroxymethylated, then methoxylated, and finally exhaustively hydroxymethylated with a large excess of formaldehyde. 4-Cyanoimino-3-methoxymethylperhydro-1,3,5-oxadiazine was isolated as a major reaction product of 1,3-bis(methoxymethyl)-2-cyanoguanidine with formaldehyde. This product is an adduct of 3 mol of formaldehyde per mole of CG and a six-membered cyclic ether. Minor products were further methoxylated and ,5-bis(methoxymethyl)-4-methoxymethyl(carbmoylimino)perhydro-1,3,5-o xadiazine was isolated. This is an adduct of 2 mol of formaldehyde to the amidinated product derived from the major product by the hydration of the cyano group.