The action of phenyllithium on some disubstituted cyanamides.

Abstract

The reactions between phenyllithium and N,Ndimethylcyanamide, N-cyanopyrrolidine (N,N-tetramethylenecyanamide), N-methyl-N-cyanoaniline (N-methyl-N-phenylcyanamide) and N,N-diphenylcyanamide have been investigated. -- 2,4-Bis(dimethylamino)-6-phenyl-1,3,5-triazine is obtained from the reaction of one part of phenyllithium and two parts of dimethylcyanamide. Isolation of the intermediates, N,N-dimethylbenzamidine and 1-(α-(dimethylamino)benzylidene)- 3,3-dimethylguanidine was successful. When the ratio is 1:4, besides 2,4-bis(dimethylamino)-6-phenyl-1,3,5- triazine, 2,4,6-tris(dimethylamino)-1,3,5-triazine is also obtained. -- The reactions between phenyllithium and Ncyanopyrrolidine at various ratio are similar to those between phenyllithium and dimethylcyanamide under the same conditions. -- The reaction between N-methyl-N-cyanoaniline and phenyllithium yields benzonitrile and 1,3-dimethyl-1,3-diphenyl-2-cyanoguanidine. The intermediate, 1,3-dimethyl-1,3-diphenylguanidine, was isolated and the mechanism of the reaction has also been suggested. -- Benzonitrile in low yield is the sole product of the reaction between phenyllithium and diphenylcyanamide. -- The spectra of the new compounds are also given.