4-Methylbenzenethiol → HCID 12945141, compound

Participants

Reaction Conditions

Reaction Steps

795 mg of O-(p-toluenesulfonyl)-p-(2-thienylcarbonyl)mandelonitrile was dissolved in 3 ml of anhydrous DMF, and the solution was stirred at -15° C. in an argon atmosphere. A solution prepared by adding 0.80 ml of a 2.5 M methanol solution of sodium methoxide at room temperature to 2 ml of an anhydrous methanol solution containing 250 mg of p-toluenethiol was added dropwise over the course of 10 minutes. After the addition, the mixture was further stirred, and its temperature was gradually raised to bring it to -5° C. in 20 minutes. At this time, an aqueous solution of ammonium chloride (1 g/30 ml) was added to the reaction mixture, and the mixture was extracted with 20 ml of methylene chloride three times. The extract was washed with 20 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethanol to afford 387 mg of alpha-[p-tolylthio)[p-(2-thienylcarbonyl)phenyl]acetonitrile as colorless crystals. The mother liquor was concentrated under reduced pressure, and the residue was separated by column chromatography (silica gel; methylene chloride) to afford 95 mg of alpha(p-tolylthio)[p-(2-thienylcarbonyl)phenyl]acetonitrile. The total amount of the products yielded was 482 mg, and the yield was 69%.

Provenance & Evidence