Iodoacetamide → 2-[5-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]acetamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of N-{5-[(4-methoxybenzyl)oxy]pyridin-2-yl}-4-methylbenzenesulfonamide (10.0 g, 26.0 mmol) in N,N-dimethylformamide (85 mL) were added N,N-diisopropylethylamine (6.8 mL, 39.0 mmol) and iodoacetamide (5.77 g, 31.0 mmol), and the mixture was stirred at 60° C. for 5 hr. After cooling to room temperature, ethyl acetate and water were added, and the mixture was extracted 3 times with a mixed solution of ethyl acetate and tetrahydrofuran. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was washed with ethyl acetate and collected by filtration to give the title compound (34.4 g, 75%) as a white solid.

Provenance & Evidence