Nicotinic Acid → HCID 20098208, compound

Participants

Reaction Steps

To a solution of 3.0 g (0.0074 mol) of 4-(3-chlorophenyl)-2-(4,6-dimethoxypyrimidin-2-ylthio)nicotinic acid in 30 ml of N,N-dimethylformamide was added 1.50 g (0.0093 mol) of carbonyldiimidazole with stirring, and the mixture was stirred at room temperature for 24 hours. To a suspension of 0.60 g (0.0015 mol) of 60% sodium hydride in 30 ml of N,N-dimethylformamide was added 1.8 g (0.0019 mol) of methanesulfonamide and stirred at 80° C. for 2 hours. Thereafter, the above prepared N,N-dimethylformamide solution of carbonylimidazole of nicotinic acid was added thereto at room temperature, and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was then poured into water, and washed with 50 ml of ethyl acetate. Thereafter, the aqueous layer was acidified with 10% HCl, and extracted with 100 ml of ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, filtrated and concentrated. The concentrate was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1/1) to obtain 3.0 g of a light-yellowish glass-like aimed product.

Provenance & Evidence