4-Methoxyphenyl isothiocyanate → 1-(2,2-Dimethoxyethyl)-3-(4-methoxyphenyl)thiourea

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A solution of 10 g (0.06 mole) of p-methoxyphenylisothiocyanate in 100 ml of CHCl3 was treated with 6.3 g (0.06 mole) of aminoacetaldehyde dimethyl acetal. The solvent was evaporated and the residue was recrystallized from ethanol to yield N-(p-methoxyphenyl)-N'-(β,β-dimethoxyethyl)thiourea, 9.2 g (57%). A suspension of this thiourea in a solution of 5 ml of concentrated H2SO4 and 20 ml of H2O was refluxed for 3 hr. The mixture was cooled and a solid was filtered, washed with H2O and dried. Recrystallization from ethanol gave 1-(4-methoxyphenyl)-2-mercaptomidazole, 4.9 g (70%), mp 215°-7°.

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