Methylamine → 4-bromo-N-methylbenzene-1-sulfonamide

Add a solution of 4-bromo-benzenesulfonyl chloride (5.0 g, 19.2 mmol) in 10 mL THF at r.t. to a solution of methylamine (9.6 ml, 2 M in THF, 19.2 mmol) and triethylamine (2.72 mL, 19.2 mmol) over a period of 60 min and stir for 18 h. Add further methylamine (9.6 ml, 2 M in THF, 19.2 mmol) and triethylamine (2.72 mL, 19.2 mmol) and stir for 18 h. Evaporate the solvent under vacuum and add dichloromethane. Wash the organic layer with saturated aqueous sodium bicarbonate solution, followed by saturated sodium chloride solution. Filter through a hydrophobic filter paper and remove the solvent under vacuum. Further purify this material via column chromatography on silica gel, eluting with a gradient of 0-50% ethyl acetate in hexane to afford the title compound (3.75 g) as a white solid. MS (m/e): 251 (M+H).

1. stirringstir for 18 h
2. customEvaporate the solvent under vacuum
3. additionadd dichloromethane
4. washWash the organic layer with saturated aqueous sodium bicarbonate solution
5. filtrationFilter through a hydrophobic filter paper
6. customremove the solvent under vacuum
7. customFurther purify this material via column chromatography on silica gel
8. washeluting with a gradient of 0-50% ethyl acetate in hexane

ORD record

ord-63ff90cc6e594e20a6690c12c59d8bdb

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576108B2