Dicyclohexylcarbodiimide → 2-(4-[(E)-hex-2-enoyloxy]phenyl)-5-pentyl-1,3,4-thiadiazole

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Reaction Steps

Dicyclohexylcarbodiimide (0.2 g) is added to a solution of 2-(4-hydroxyphenyl)-5-pentyl-1,3,4-thiadiazole [Mol. Cryst. Liq. Cryst., (1990) Vol., 191, pp 223] (0.25 g), (E)-hex-2-enoic acid, (0.1 g) 4-(dimethylamino)pyridine (0.05 g) and dichloromethane (20 cm3) at 0° C. under an atmosphere of nitrogen. The reaction mixture is stirred overnight at room temperature, filtered to remove inorganic material and the filtrate evaporated down. The residue is purified by column chromatography on silica gel using hexanelethyl acetate (9/1 v/v) as eluent and recrystallisation from hexane to yield 0.17 g of 2-(4-[(E)-hex-2-enoyloxy]phenyl)-5-pentyl-1,3,4-thiadiazole.

Provenance & Evidence