Thionyl Chloride → 2-[2-(3-Methoxypropylamino)benzylthio]imidazole

Participants

Reaction Steps

To a solution of 2.9 g (14.8 mmol) of 2-(3-methoxypropyl) aminobenzyl alcohol in 29 ml of dichloromethane was dropwise added a solution of 1.3 ml (17.8 mmol) of thionyl chloride in 3 ml of dichloromethane under chilling with ice for a period of 5 min. The resulting mixture was stirred for 15 min. at room temperature. The solvent was distilled off under reduced pressure at room temperature. To the residue was added 10 ml of dichloromethane. The obtained dichloromethane solution was little by little added to a solution of 2.22 g (22.2 mmol) of 2.mercaptoimidazole in 22 ml of ethanol, and then the mixture was stirred for 15 min. at room temperature. Ethanol was distilled off under reduced pressure. To the residue were added ice and saturated aqueous sodium hydrogencarbonate. The resulting mixture was treated with ether for extraction. The organic portion was collected and sequentially washed with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 2.7 g of the desired compound as a pale yellow oil. (Yield: 65.8 %)

Provenance & Evidence