Methylamine → N-methyl-2-nitrobenzene-1-sulfonamide

To a solution of 2-nitrobenzenesulfonyl chloride (25 g, 0.113 mol) and dichloromethane (450 mL) at 4° C. was added dropwise 2M methylamine in tetrahydrofuran (68 mL). The mixture was stirred overnight allowing the ice bath to melt. More 2M methylamine in tetrahydrofuran (97 mL) was added and the reaction was stirred for 1 hour. The reaction mixture was concentrated in vacuo. The residue was dissolved in chloroform (500 mL) and was washed with saturated sodium bicarbonate (250 mL). The aqueous layer was extracted with chloroform (250 mL) and all the chloroform layers combined, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue purified by silica gel chromatography using 0-4% methanol in dichloromethane. 22.63 g of N-methyl-2-nitrobenzenesulfonamide was obtained.

1. stirringthe reaction was stirred for 1 hour
2. concentrationThe reaction mixture was concentrated in vacuo
3. dissolutionThe residue was dissolved in chloroform (500 mL)
4. washwas washed with saturated sodium bicarbonate (250 mL)
5. extractionThe aqueous layer was extracted with chloroform (250 mL) and all the chloroform layers
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated in vacuo
9. customthe residue purified by silica gel chromatography

ORD record

ord-4e6a4e89cb304485baec965320cb4319

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06884801B1