The synthesis of some phosphorylated ethyl carbamates



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In an effort to further investigate the effects of phosphorusnitrogen bonding in the coupling of organotropic with cytotoxic groupings, a series of N-phosphorylated urethans has been prepared. These derivatives were synthesized as potential carcino-chemotherapeutic agents in an attempt to enhance the selectivity of action of the parent moiety. Also, it was felt that should any of these compounds exhibit activity against experimental tumors, the concept of "dual antagonists" for a series of similar compounds would find additional support. The phosphorylated ethyl carbamates were prepared from dichlorophosphoroisocyanatidate and a second intermediate, dichlorophosphinylurethan. The reaction between phosphorus pentachloride and urethan was used to prepare the isocyanate, and subsequent reaction of this compound with absolute ethanol yielded an in situ preparation of dichlorophosphinylurethan. This compound was then reacted with four equivalents of a primary amine to yield the phosphorylated ethyl carbamates. In the attempted preparation of a carbamate, ethyl-[bis(4-morpholino)phosphinyl]-carbamate, a carbamide, 4-[N-(dimorpholinophosphinyl)carbamoylj-morpholine, was isolated as a principal product. The compounds prepared were characterized by melting points, elemental analyses, and infrared absorption spectra. The ethyl carbamates prepared were the dianilinophosphinyl, di-p-toluidinophosphinyl, diaminophosphinyl, bis(cyclohexyl)phosphinyl, bis(2-pyridylamino)phosphinyl, and bis(phenylhydrazino)phosphinyl derivatives.