Pyridine → 2-Amino-5-[(methylsulfonyl)amino]benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

2,5-Diaminobenzenesulfonamide (14.5 g, 77.2 mmol) was dissolved in acetonitrile (150 mL) and pyridine (9.37 mL, 115.9 mmol) was added. Methanesulfonyl chloride (6.28 mL, 81.1 mmol) was added dropwise over a period of 15 min and the reaction mixture was stirred for 20 h at 25° C. after which time a precipitate had formed. Most of the acetonitrile (approximately 110 mL) was removed in vacuo and water (120 mL) was added to afford a clear solution. A purple solid precipitated from this solution over the next 2 h. This precipitate was collected by vacuum filtration, washed with methyl-tert-butyl ether (3×30 mL) and dried in vacuo overnight at 50° C. to afford the desired product, 2-amino-5-methanesulfonylamino-benzenesulfonamide (also made in Example 1d) (18.2 g, 68.7 mmol, 89%) as a purple solid. 1H NMR (400 MHz, CD3OD) δ: 2.89 (3H, s), 6.82 (1H, d, J=8.5 Hz), 7.20 (1H, dd, J1=8.5 Hz, J2=2.5 Hz), 7.58 (1H, d, J=2.5 Hz). LC-MS (ESI) calcd for C7H11N3O4S2 265.02, found 266.0 [M+H+].

Provenance & Evidence