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

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,5-diamino-benzenesulfonamide (0.288 g, 0.0015 mol, 1 eq.), dichloromethane (5 mL), and pyridine (5 mL) was stirred at 0° C. Methanesulfonyl chloride (119 μL, 0.0015 mol, 1 eq.) was added dropwise over 3 minutes. The reaction mixture was warmed to 25° and stirred for 18 hours. The reaction mixture was evaporated under reduced pressure and the residue was chromatographed on silica gel using a step gradient of 0-4% methanol in dichloromethane to yield 2-amino-5-[(methylsulfonyl)amino]benzenesulfonamide (68% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.87 (s, 3 H) 3.39 (s, 1 H) 5.80 (s, 1 H) 6.78 (d, J=8.82 Hz, 1 H) 7.13 (dd, J=8.64, 2.39 Hz, 1 H) 7.29 (s, 2 H) 7.45 (d, J=2.57 Hz, 1 H) 9.21 (m, 1 H). MS (ESI m/z=266 (M+H)+.

Provenance & Evidence