Hydrochloric Acid → 4-(chloromethyl)-N-methylbenzamide

To a solution 4-(chloromethyl)benzoyl chloride (1.0 g, 5.29 mmol) and methylamine.HCl (1.0 g, 5.80 mmol) in dichloromethane (40 mL) was added DIPEA (2.01 g, 15.6 mmol) at 0° C. and stirred for 1 h. The reaction mixture was extracted with water (1×50 mL). The organic layer was extracted with brine (1×50 mL), dried over Na2SO4 and the solvent was removed under reduced pressure to afford 1.0 g (quantitative) of 4-(chloromethyl)-N-methylbenzamide (I-30) as an off white solid. 1H NMR (400 MHz, DMSO) δ 8.46 (d, J=3.5 Hz, 1H), 7.82 (d, J=8.4 Hz, 2H), 7.51 (d, J=8.3 Hz, 2H), 4.80 (s, 2H), 2.78 (d, J=4.4 Hz, 3H); ESI-LC/MS (m/z): [M+H]+ 184.2, RT 2.46 min.

1. extractionThe reaction mixture was extracted with water (1×50 mL)
2. extractionThe organic layer was extracted with brine (1×50 mL)
3. dry with materialdried over Na2SO4
4. customthe solvent was removed under reduced pressure

ORD record

ord-661250e031c54bb3b68bed85ac490e99

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871754B2