Acetone → HCID 46842202, compound

Participants

Reaction Steps

2-Mercaptobenzothiazole (4.1 g) was added to a solution of sodium hydroxide (1.0 g) in water (20.0 mL). The reaction mixture was stirred for 15 minutes, while maintaining the temperature of 25˜35° C. Acetone (36.0 mL) and N-[5-chloromethyl-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide (9.0 g) were added to the reaction mixture, which was then stirred for 3 hours, while maintaining the temperature of 25˜35° C. The reaction was monitored with thin layer chromatography (ethyl acetate/n-hexane=1:3). The reaction mixture was cooled to 20˜25° C. and then water (45.0 mL) was added thereto. The separated organic layer was concentrated under reduced pressure to remove the solvent. Dichloromethane (90.0 mL) was added to the resulting residue, which was then cooled to 0˜5° C. m-Chloroperbenzoic acid (13.5 g) was added to the reaction mixture, which was then stirred at 0˜5° C. for 2 hours. The reaction was monitored with thin layer chromatography (ethyl acetate/n-hexane=1:3). The temperature of the reaction mixture was adjusted to 20˜25° C. 10% Sodium sulfite solution (90.0 mL) was added to the reaction mixture under stirring. The separated organic layer was sequentially washed with 8% sodium bicarbonate solution (90.0 mL) and water (90.0 mL), and then concentrated under reduced pressure to remove the solvent. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1:3) to obtain N-[5-benzothiazol-2-sulfonylmethyl-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide as a white solid (10.9 g, yield 84%).

Provenance & Evidence