Benzyl mercaptan → HCID 23226996, compound

Participants

Reaction Steps

A solution of 6.7 g of impure 5-(2,2-dimethyl-1-indanyl)-4-methanesulfonylpyrimidine (approximately 6.1 g (0.20 mol) in 50 mL of dry tetrahydrofuran was prepared and to this was added with stirring 2.5 mL (2.6 g, 0.21 mol) of benzyl mercaptan and then, in several small portions, 0.84 g of 60 percent sodium hydride in mineral oil (0.21 mol). Hydrogen was evolved and the mixture became cloudy. After about 4 hr the mixture was diluted with 200 mL of hexane and 150 mL of 2N aqueous sodium hydroxide. The phases were separated and the organic phase was washed with water, dried over sodium sulfate, and concentrated by evaporation under reduced pressure to obtain 7.6 g of crude product. This was dissolved in hexane and flash chromatographed on silica gel eluting first with hexane (10×200 mL) and then with a 25:75 by volume mixture of dichloromethane and hexane (14×200 mL) and then with dichloromethane 12×200 mL). There was desired product in fractions 12-36 and these fractions were combined and the resulting mixture was concentrated by evaporation under reduced pressure at 50° C. to obtain 6.3 g of the title compound as a white solid melting at 76°-79° C.

Provenance & Evidence