Methylamine → 3-bromo-N-methylbenzene-1-sulfonamide

To a solution of 3-bromobenzenesulfonyl chloride (2.5 g, 11.2 mmol) in THF (15 mL) at 0° C. was added methylamine (2.0 M in THF; 28 mL, 56 mmol). The resulting solution was allowed to warm to room temp. and was stirred at room temp. overnight. The resulting mixture was separated between EtOAc (25 mL) and a 1 M HCl solution (25 mL). The aqueous phase was back-extracted with EtOAc (2×25 mL). The combined organic phases were sequentially washed with water (2×25 mL) and a saturated NaCl solution (25 mL), dried (MgSO4) and concentrated under reduced pressure to give N-methyl-3-bromobenzenesulfonamide as a white solid (2.8 g, 99%).

1. temperatureto warm to room temp.
2. customThe resulting mixture was separated between EtOAc (25 mL)
3. extractionThe aqueous phase was back-extracted with EtOAc (2×25 mL)
4. washThe combined organic phases were sequentially washed with water (2×25 mL)
5. dry with materiala saturated NaCl solution (25 mL), dried (MgSO4)
6. concentrationconcentrated under reduced pressure

ORD record

ord-1c8365b710764efca9fb600eaa2c80d1

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841330B2