Triazine isocyanates: Part II: Reaction of 2,4-diamino-s-triazines with ethyl chlorocarbonate

Benzoguanamine (2,4-diamino-6-phenyl-s-triazine) and acetoguanamine (2,4-diamino-6-methyl-s-triazine) both react with an excess of ethyl chlorocarbonate; in this reaction two hydrogen atoms from the guanamines are replaced by two carbethoxy groups. The I.R. spectrum reveals that this double substitution takes place on one amino group; in consequence, the resulting compounds are derivatives of iminodicarboxylic acid diethyl ester. Upon heating above the melting point, the compounds decompose, during which process a very short occurrence of isocyanate absorption can be observed in the I.R. spectrum.