Alkylation reactions of hydantoins and succinimides

Five anticonvulsant agents, namely, diphenylhydantoin, mephenytoin, ethotoin, ethosuximide, and phensuximide, and a number of other hydantoins were investigated in their reactions with p‐ and m‐nitrobenzyl bromides in the presence of sodium carbonate. The structures of the alkylation derivatives and other products formed in the reactions were studied. On the basis of the melting points of the alkylation derivatives, it was possible to identify and differentiate the five anticonvulsants. 3‐p‐Nitrobenzyl‐5,5‐diphenylhydantoin, N‐p‐nitrobenzyl‐2‐ethyl‐2‐methylsuccinimide, and 3,3′‐diethyl‐5,5′‐diphenylhydantil, at a dose of 1 g./kg. given orally, provided no protection against pentylenetetrazol‐induced seizures in mice.