R. D. Sagher, J. Pocius, J. Thénot
Aug 1, 1978
Citations
0
Influential Citations
9
Citations
Journal
Journal of Chromatography A
Abstract
Abstract The rate of alkylation of 3-ethyl-5,5-diphenylhydantoin in aqueous acetone at room temperature was found to decrease in the order methyl > ethyl > n -propyl, consistent with an S N 2 mechanism. The reactivity of the N 1 nitrogen atom is influenced by the substituent at C 5 , and it was observed that 5-ethyl-5-phenylhydantoin (Nirvanol) reacts more slowly than 5,5-diphenylhydantoin (phenytoin). Derivatization conditions were optimized for the perethylation of 5,5-disubstituted hydantoins, as ethylation is sufficient to separate 3-methyl-5-ethyl-5-phenylhydantoin (mephenytoin) from its N-demethylated metabolite (Nirvanol) on an SE-30 column.