Syntheses of Acryloguanamine and Methacryloguanamine

Abstract

Syntheses of acryloguanamine (vinyl-1, 3, 5-triazine) and methacryloguanamine- (isopropenyl-1, 3, 5-triazine) by the reaction of unsaturated carboxylic derivatives with biguanide were inves-tigated in detail. Acryloguanamine was generally obtained in low yield from acrylic derivatives except acrylic anhydride. Alkyl methacrylates gave methacryloguanamine in satisfactory yield when it was treated with phenylbiguanide in such a dipolar aprotic solvent as dimethyl sulfoxide (DMSO) in the presence of sodium hydride. Further, it was rapidly obtained in 80-90% yield at a low temperature when such an active ester as phenyl or p-nitrophenyl metha-crylate was used. And also a pure methacryloguanamine was prepared in approximately quantitative yield in DMSO for 15 minutes by using methacrylic anhydride. On the other hand, it was found that a acrylo- or methacryloguanamines were readily synthesized by the reaction of acrylic or methacrylic acid with phenylbiguanide when using cyanuric chloride as an activating agent. By means of the above synthetic procedure, various methacryloguanamines, substituted by methyl and phenyl groups, were prepared in adequate purity and high yield.