Methylamine → 5-chloro-2,N-dimethylbenzamide

Participants

Reaction Steps

5-Chloro-2-methylbenzoic acid (9.16 g, 53.7 mmol) and thionyl chloride (25.6 g, 15.7 ml, 215 mmol) were heated at reflux temperature for 1.5 h. Solvent was evaporated under reduced pressure and the residue dissolved in DCM (55 mL). Methylamine (aq.) (40%) (12.51 g, 13.90 mL, 161 mmol) was added dropwise at 0° C. The reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was extracted with EtOAc (50 mL), washed with brine (50 mL), dried (Na2SO4) and evaporated in vacuo to afford 5-chloro-2,N-dimethylbenzamide (8.79 g, 47.9 mmol, 89%) as a white solid. This was used directly in the next stage without purification

Provenance & Evidence