Methanol → alpha-(2-Benzothiazolylthio)(m-benzoylphenyl)-acetonitrile

Participants

Reaction Steps

Methanol (6 ml) and 3 ml of DME were added to 1.18 g of O-(p-toluenesulfonyl)-m-benzoylmandelonitrile, and the mixture was stirred in an argon atmosphere under ice cooling. Sodium salt of 2-mercaptobenzothiazole (570 mg) was added, and the mixture was stirred for 1.5 hours under ice cooling. Water (50 ml) was added, and the mixture was extracted with 30 ml of methylene chloride three times. The extract was washed with 40 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (silica gel; methylene chloride) to afford 972 mg (yield 83%) of alpha-(2-benzothiazolylthio)-(m-benzoylphenyl)acetonitrile as a pale yellow oil.

Provenance & Evidence