An Overview of Synthesis of 5,5-Diphenyl-2,4-imidazolidinedione from Almond and Some Synthesis of 5-(alk-3-enyl)-2,4-imidazolidinediones

Mohammad Asif


The synthesize of 5,5-diphenyl-2,4-imidazoli-dinedione (Phenytoin) from almond kernels as starting materials which were ground then, through steam distillation and extraction methods, almond oil and subsequently benzaldehyde were isolated and purified. Benzaldehyde react with sodium cyanide in presence of aqueous alcohol undergone a dimolecular condensation product, benzoin. Oxidation of benzoin yielded benzil. Benzil reacted with urea in basic alcoholic solution first gave benzilic acid, and then a condensation reaction with urea and after acidification of the filtrate gave phenytoin. Construction of 5-(alk-3-enyl)-hydantoins start from unsaturated carbonyl compounds, like aldehydes, ketones and ß-ketoesters, by multi component Bucherer-Bergs reaction conditions. Some of them were acetylated at N(1) position with acetanhydride. When a-allyl-ß-ketoesters were used as substrate an unexpected decarboxylation was observed. Decarboxylation was not observed only when 2-allyl-ethylacetoacetate was used for synthesis of hydantoin while in other cases fully decarboxylated products were obtained.


Benzaldehyde, Benzoin, Benzil, 2,4-imidazolidinedione, Phenytoin, Bucherer-bergs reaction, Hydantoins, Acetylation, Decarboxylation

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