Synthesis and properties of pyrimidinylalkylsulfonamides 4. Reaction of the Na salt of p-toluenesulfonamide with mono-N-(ω-haloalkyl)uracils

Conclusions The direction of reaction and the composition and yields of products obtained by reaction of the Na salt of p-toluenesulfonamide with N-(-bromoalkyl)uracils depend primarily on the length of the alkyl chain in the latter: When the Na salt of p-toluenesulfonamide reacts with N-(-bromopropyl)-6-methyluracil, the latter undergoes intramolecular cyclization, whereas the Na salt of p-toluenesulfonamide undergoes intermolecular alkylation at the sulfonamide group on reaction with N-(-bromopentyl)-6-methyluracil. In analogous reactions, N-(-bromobutyl)uracils undergo both intramolecular cyclization, followed by opening of the oxazepine ring by nucleophilic reagents, and intermolecular alkylation.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2079–2084, September, 1978.