Methyl iodide → alpha-(2-Benzothiazolylthio)-alpha-(m-benzoylphenyl)propionitrile

Participants

Reaction Steps

1.18 g of O-(p-toluenesulfonyl)-m-benzoylmandelonitrile was dissolved in a mixture of 4 ml of methanol and 3 ml of DME, and the solution was stirred in an argon atmosphere under ice cooling. Sodium salt of 2-mercaptobenzothiazole (570 mg) was addded, and the mixture was stirred for 1 hour under ice cooling. Then, 1.15 ml of a 2.7 M methanol solution of sodium methoxide was added, and 0.22 ml of methyl iodide was further added dropwise. The temperature was brought to room temperature, and the solution was stirred for 1 hour. An aqueous solution of ammonium chloride (1 g/20 ml) was added, and the mixture was extracted with 40 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; benzene and methylene chloride) to afford 892 mg (yield 74%) of alpha-(2-benzothiazolyl-thio)-alpha-(m-benzoylphenyl)propionitrile.

Provenance & Evidence