N-(1,1,3-trioxo-1,2,3,4-tetrahydro-1lambda6-benzo[1,2,4]thiadiazin-7-yl)-methanesulfonamide → 2-Amino-5-[(methylsulfonyl)amino]benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

N-(1,1,3-Trioxo-1,2,3,4-tetrahydro-1λ6-benzo[1,2,4]thiadiazin-7-yl)-methanesulfonamide (Example 3c, 1 g, 3.4 mmol) was suspended in 12 M aqueous hydrochloric acid solution (60 mL). The mixture was stirred at 105° C. for 16 h. All solids were dissolved at this point. The mixture was diluted with water (250 mL). The solution was concentrated in vacuo to an orange solid. The solid was dissolved in water (20 mL) and concentrated in vacuo to an orange solid. The solid was dissolved in water (5 mL) and the product was extracted into ethyl acetate (6×20 mL). The combined organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to an orange solid. Purification by flash column chromatography (Merck silica gel 60, 40-63 μm, 75% ethyl acetate in hexanes) afforded the desired product, 2-amino-5-methanesulfonylamino-benzenesulfonamide (0.41 g, 1.55 mmol, 45% yield), as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ 2.86 (3H, s), 5.77 (2H, s), 6.76 (1H, d, J=8.6 Hz), 7.11 (1H, dd, J1=8.6 Hz, J2=2.4 Hz), 7.25 (2H, bs), 7.43 (1H, d, J=3.1 Hz), 9.16 (1H, s).

Provenance & Evidence