Lateral lithiation and substitution of N'-(2-methylphenyl)-N,N-dimethylurea

Abstract

Lithiation of N'-(2-methylphenyl)-N,N-dimethylurea with three molar equivalents of tert-butyllithium at 40 to 30 C takes place on the nitrogen and on the methyl group at position 2 of the phenyl group. The lithium intermediate thus obtained reacts with a variety of electrophiles to give the corresponding side-chain substituted derivatives in high yields.