Reaction #473473

Reaction equation

2-amino-4-chlorobenzonitrile

pyridine

PhCOCl

→

title compound

N-(5-Chloro-2-cyanophenyl)benzamide

Solvents

DCM

Conditions

Workup

1. 1
   WashThe reaction mixture was washed (H2O, 2 M aq HCl (2×), H2O, brine)
2. 2
   Dryingdried (Na2SO4)
3. 3
   Concentrationconcentrated under reduced pressure

Procedure

To a solution of 2-amino-4-chlorobenzonitrile (7.25 g, 47.5 mmol), in anh. pyridine (38 mL, 475 mmol) and DCM (300 mL) cooled in an ice-H2O bath under Ar was added PhCOCl (5.8 mL, 50 mmol) dropwise. The reaction was allowed to slowly warm to rt within the cooling bath and then was stirred at rt overnight. The reaction mixture was washed (H2O, 2 M aq HCl (2×), H2O, brine), dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as a white solid; MS (ES+): m/z 257.1 (100) [MH+]; HPLC: tR=3.27 min (OpenLynx, polar—5 min).

Source