The reaction of cyanoguanidine with formaldehyde. I. Hydroxymethylation and methoxymethylation of cyanoguanidine.

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  • ChemInform Abstract: THE REACTION OF CYANOGUANIDINE WITH FORMALDEHYDE. I. HYDROXYMETHYLATION AND METHOXYMETHYLATION OF CYANOGUANIDINE

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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 3,5-bis(methoxymethyl)-4-methoxymethyl(carbamoylimino)perhydro-1,3,5-oxadiazine 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. The ring structure of perhydro-1,3,5-oxadiazine was so stable that it could not be decomposed under acidic conditions if the methoxymethyl groups were fully acid-hydrolyzed.

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