Chloroform → HCID 13320313, compound

Participants

Reaction Steps

A solution of 1-(2,2-diethoxyethyl)-1H-imidazole (3.68 g, 0.020 mole), 4-chlorothiophenol (2.88 g, 0.020 mole) and 4-chlorobenzyl mercaptan (3.16 g, 0.020 mole) in chloroform (50 ml) was added dropwise during 30 minutes to a stirred, refluxing mixture of boron trifluoride etherate (4.8 ml, 0.036 mole) and acetic acid (10 ml) in chloroform (30 ml). The mixture was stirred under reflux for 18 hours and concentrated. The residue was partitioned between diethyl ether and cold aqueous sodium hydroxide. The organic layer was washed with water (2×) followed by brine and dried over Na2SO4. Hydrogen chloride was bubbled into the ethereal filtrate to afford a mixture of the hydrochloride salts of the three possible mercaptals. The mixture was crystallized from ethanol-ether to yield 1.4 g of 1-[2,2-bis(4-chlorobenzylthio)ethyl]-1H-imidazole hydrochloride, mp 180°-183°. Dilution of the mother liquor with additional ether provided 2.2 g of the title compound, mp 135°-137°, which melted at 136°-139° after recrystallization from chloroform-ether.

Provenance & Evidence