Sintesis Senyawa 5-(4'-klorobenzilidena)imidazolina-2,4-dion

Abstract

5-Benzalhydantoin or 5-benzylidene-imidazolidine-2,4-dione (3)derivatives have been isolated from marine red sponge Laxosubrites sp. as bioactive compounds. They also have been synthesized many decades ago, as an anticonvulsants, antiviral, inhibitor of EGFR and A431 cell antiproliferative, anti-cancer HepG2 cells, antimetastatic cancer PC-3M cells, inhibitors of the tyrosinase enzyme and melanin formation, as well as in agriculture as herbicides and fungicides. The aim of this study were to synthesis 5-(4'-cholrobenzylidene)-imidazolidine-2,4-dione (7)from hydantoin (1)and 4-chlorobenzaldehyde (2), using sodium bicarbonate in water or ethanol and ethanolamine as catalyst (modification of Eli Lily’s methods). The precursor of the reaction (hydantoin (1)and 4-chlorobenzaldehyde (2)) were obtained commercially. First of all, hydantoin (1)is reacted with 4-chlorobenzaldehyde (2)stochiometrically and fused with ethanolamine as base catalyst in this reaction in ethanol and water. The reaction was carried out under reflux condition for 6 hours. The obtained compound is then purified from hot ethanol to give a pure white needle crystal. The yield of 5-(4'-cholrobenzylidene)-imidazolidine-2,4-dione was obtained 12 %. The compound was analysed by using silica gel GF254with TLC procedure (acetone-hexane 1:1 v/v) and Rf = 0,625, Melting point (Mp)=292-294°C (Mp Lit.=294-296°C). The identification of obtained compound is done with UV, IR, HR-TOF-MS ES+, 1H-NMR dan 13C-NMR, and the results are showed a consistency with the target molecule, means 5-(4'-chlorobenzylidene)-imidazolidine-2,4-dione (7)is succesfully synthesized.