N3-Monomethylation of Phenytoin
Ridha Agustina Kholifatun Nisa,a) Fahimah Martak,b) and Arif Fadlan,c)

Department of Chemistry, Faculty of Science and Data Analytics, Institut Teknologi Sepuluh Nopember

Abstract

Structural modification of phenytoin, a major antiepileptic drug with imidazole framework, can be performed by alkylation, arylation, and halogenation at N1-, N3- and C5. The N3- alkylation can be achieved more than N1- due to its higher acidity. A methyl group influences the biological activity of active compounds. In this work, the N3-monomethylation of phenytoin was carried out by using potassium tert-butoxide and iodomethane in acetonitrile and afforded 3-methyl-5,5-diphenylimidazolidine-2,4-dione. The methylation has been preceded by synthesis of benzoin, benzil, and phenytoin. The resulted compounds were characterized based on the spectroscopic methods (NMR, MS, infrared).

Keywords: methylation, phenytoin, alkylation

Topic: Organic Chemistry