Reaction of cyanuryl chloride and some of its monosubstituted derivatives with toluene

The Friedel-Crafts reaction of cyanuryl chloride and some of its monosubstituted derivatives with toluene was studied. It is shown that the type and character of the substituent in the 6 position of the starting derivatives of cyanuryl chloride have a strong effect on the course of the reaction. The reaction of cyanuryl chloride and its phenyl and phenoxy derivatives with toluene leads smoothly to the formation of 2,4,6-tris- and 2-substituted 4,6-bis(4-methylphenyl)-sym-triazines. 4,6-Bis(4-methylphenyl)2-oxo-2,3-dihydro-sym-triazine is formed in the case of alkoxy-substituted cyanuryl chlorides. In the case of amino derivatives of cyanuryl chloride the reaction with toluene takes place only upon prolonged refluxing and gives the final products in low yields.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 558–561, April, 1979.