Phenyl chloroformate → Phenyl (4-cyano-3-(4-nitrophenyl)isothiazol-5-yl)carbamate

Participants

Reaction Steps

To a mixture of 5-amino-3-(4-nitrophenyl)isothiazole-4-carbonitrile (394 mg, 1.60 mmol), N,N-diisopropylethylamine (0.836 mL, 4.8 mmol), and catalytic DMAP in 20 mL 1,2-dichloroethane at rt was added phenyl chloroformate (0.301 mL, 2.40 mmol) drop wise over 1 minute. The reaction mixture was stirred at rt for 22 hours, then added directly to a dry packed silica gel column eluting with CHCl3, then gradient 10% to 50% EtOAc in CHCl3. The title compound was obtained as a beige solid (131 mg, 22%) and used as is for the next step.

Provenance & Evidence