Cytotoxic compounds. Part X. Carbamates derived from NN-bis-(2-chloroethyl)-m- and NN-bis-(2-chloroethyl)-p-phenylenediamine

Abstract

Urethanes have been prepared by reaction of the amines m-RNH₂ or p-RNH₂[R = C₆H₄·N(CH₂·CH₂Cl)₂] with chloroformates. The products, after removal of protecting groups, include p-RNH·CO·O·C₆H₄·CO₂H (o-, m-, and p-), m-RNH·CO·O·C₆H₄·CO₂H(m-), O-(p-RNH·CO)-serine, and O-(p-RNH·CO)-threonine. Terephthalic amides, (p-RNH·CO)₂C₆H₄ and (p-RNH·CO)C₆H₄·CO₂Me, and phthalimides, C₆H₄(CO)₂NR (m- and p-), are also described.