Sulfuric Acid → HCID 178491962, compound

Participants

Reaction Steps

A solution of 10 g (.06 mole) of p-methoxyphenyl isothiocyanate in 100 ml of CHCl3 was treated with 6.3 g (.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 hours. 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° . The compound can be deprotected, for example, as illustrated in Example 5 and 6, below, to prepare the phenol, Y is --OH.

Provenance & Evidence