Chloroacetamide → 1-(Carbamylmethyl)-5-iodo-2-(p-toluenesulfonamido)pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of the product (1.60 g, 4.27 mmol) from Step A in 8.0 mL of dry N,N-dimethylformamide was added sodium hydride (188 mg of 60 weight % dispersion in mineral oil, 4.44 mmol). After 15 min, the solution was warmed to 60° C. for 10 min, and was then cooled to room temperature. Chloroacetamide (420 mg) was added in one portion, and the solution was then warmed to 100° C. After 2.5 h, the solution was cooled to room temperature and poured into 70 mL of ice-water. The resultant precipitate was collected, washed with water and air-dried overnight. The crude product was subsequently stirred with 20 mL of methanol for several minutes, and the product was collected by filtration to afford the title compound as a white powder. LC/MS 414.9 (M+1-H2O).

Provenance & Evidence