THE PREPARATION OF N,N′-BIS-(p-SUBSTITUTED PHENYL)-α,ω-POLYMETHYLENEDIAMINES

A series of α, ω-bis-(p-aminophenoxy)-alkanes were found to show schistosomicidal activity against experimental animals, but having toxic effect. Based upon the fundamental chemical skeleton, we designed the following type: to study the relationship between their chemical constitution and schistosomicidal activity. N, N'-bis-(p-substituted phenyl)-α,ω-polymethylenediamines were prepared by the condensation of the sodium salts of p-substituted p-toluenesulfonanilides with α, ω-dibromoalkanes, followed by hydrolysis with hydrobromic acid and phenol. But the two bromo compounds were obtained by hydrolysis with hydrochloric acid, since treatment with hydrobromic acid possibly resulted in the loss of the nuclear bromine atoms. Among this series, N, N'-bis-(p-halo-phenyl)-α, ω-heptanediamine were also prepared by the direct condensation of the corresponding p-substituted anilines with α, ω- dibromoheptane in alcoholic solution.