Abstract
N, N'-Di-p-acetoxybenzoylmelamine (4) was synthesized from melamine and p-acetoxybenzoic anhydride in dioxane through the intermediate, N p-acetoxybenzoylmelamine (1). Upon hydrolysis with 5% aqueous ammonia, (1) and (4) gave N-p-hydroxybenzoyl melamine (3) and N, N'-di-p-hydroxybenzoylmelamine (5), respectively. (3) was also obtained by hydrolyzing the N', N"-diacetyl derivative (2) of (1). The crude product obtained from (4) and p-acetoxybenzoic anhydride in dioxane was hydrolyzed to give N, N', N"-tri-p-hydroxybenzoylmelamine (6). A dye (DS→(3)) was formed when diazotized sulf anilic acid (DS) was coupled with (3) in the presence of pyridine, although the yield was low. However, when diazotized p-nitroaniline-o-sulf onic acid was used, an abnormally coupled product was formed. In order to eliminate the undesired reaction, the N', N"-diphenyl derivative (8) of (3) which had been prepared from the N', N"-diphenyl derivative (7) of (1) through hydrolysis was used for the coupling reaction to obtain the expected product in good yield. None of the compounds (1) through (8) had previously been reported in the literature.
