Diethylcarbamoyl chloride → HCID 178464342, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (4Z)-6-iodo-4-{[(3-hydroxy-4-methoxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione (0.30 g, 0.67 mmol) in 3 mL of N,N′-dimethylformamide and 2 mL of pyridine is added diethylcarbamylchloride (0.10 mL, 0.80 mmol) and 0.21 mL (2.00 mmol) of triethylamine. The reaction mixture is stirred at 80° C. for 4 h and then at room temperature over weekend under N2. Mass spectroscopy suggested the completion of reaction. The reaction mixture is concentrated, and 2 mL of MeOH is added to break up the solid, followed by addition of excess amount of Et2O. The precipitate is filtered, washed successively with water, methanol, ether and hexane, and dried in oven (60° C.) overnight to afford 0.207 g (56.6% yield) of tan solid: mp 128-130° C.; MS (ESI) m/z 548.2 (M−H)−1

Provenance & Evidence