Methylamine → 5-chloro-2,N-dimethylbenzamide

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

1. temperatureat reflux temperature for 1.5 h
2. customSolvent was evaporated under reduced pressure
3. dissolutionthe residue dissolved in DCM (55 mL)
4. extractionThe reaction mixture was extracted with EtOAc (50 mL)
5. washwashed with brine (50 mL)
6. dry with materialdried (Na2SO4)
7. customevaporated in vacuo

ORD record

ord-d6d9a29f07e0436c853e6548da22fa62

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07820649B2