Epichlorohydrin → 2-[4-(2,3-Epoxypropoxy)-phenyl]-thiazole

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Reaction Steps

0.5 g of 2-(4-hydroxyphenyl)-thiazole is added in one portion to a mixture, heated under reflux, of 5 ml of epichlorohydrin and 0.79 g of potassium carbonate and the reaction mixture is then heated under reflux for a further 20 minutes. After cooling, the mixture is filtered, the filtrate is concentrated by evaporation in a rotary evaporator and the residue is dissolved in 6 ml of dichloromethane; 100 mg of tetrabutylammonium hydrogen sulphate and 6 ml of 2N sodium hydroxide solution are added to the solution and the whole is stirred for 3 hours at room temperature. The organic phase is separated off, washed with water and dried over sodium sulphate and the solvent is then removed in a rotary evaporator. The residue is recrystallised from a mixture of ether/hexane, yielding 2-[4-(2,3-epoxypropoxy)-phenyl]-thiazole having a melting point of 82°-93°.

Provenance & Evidence