Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 5,6-Bis(4-methoxyphenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole

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Reaction Steps

To a stirred slurry of 3.1 g (0.01 mole) 4,5 bis-(p-methoxyphenyl)-2-mercaptoimidazole [Anschutz and Schwickerath, Ann., 284, 24 (1895)] in 50 ml methanol was added 0.65 g (0.012 mole) of sodium methoxide. To the resulting solution was added 2.6 g (0.011 mole) 2-chloroethyl-p-toluenesulfonate in 10 ml methanol. The mixture was heated at reflux overnight. Another 0.5 g (0.002 mole) of 2-chloroethyl-p-toluenesulfonate was added and refluxing was continued another 2 hours. The mixture was poured into ice water and extracted with methylene chloride three times. The methylene chloride layers were dried and concentrated on a rotary evaporator. The residue was chromatographed on silica gel, eluting with chloroform. The product was obtained by trituration of fractions 4 and 5 with ether to give crystalline material, m.p. 149°-151°. Analysis by IR, NMR and CHN microanalysis indicated the product in a purity of about 85%.

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