Synthesis of 5,5-Diphenyl-2,4-imidazolidinedione (Phenytoin) from Almond

Abstract

In present studies, it is proposed to synthesized phenytoin from the easily accessible starting materials which are available in Iran. Almond kernels were ground then, through steam distillation and extraction methods, almond oil and subsequently benzaldehyde were isolated and purified. Benzaldehyde under the influence of sodium cyanide in aqueous alcohol undergone a dimolecular condensation reaction and gave benzoin. Oxidation of benzoin with concentrated nitric acid yielded benzil. Benzil on treatment with urea in alcoholic solution in presence of NaOH (30 %) first gave benzilic acid, then through a condensation reaction with urea and after acidification of the filtrate with HCl (2 M) gave 5,5-diphenyl- 2,4-imidazoli-dinedione (Phenytoin). The chemical structures of the intermediates and products were determined through their IR, ¹H NMR and MS (EI) spectra.