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

Temperature

23 °C

2,5-Diamino-benzenesulfonamide methanesulfonate (1.80 kg, 6.35 mol) was suspended in acetonitrile (24 L). Pyridine (1.55 L, 19.1 mol) was added, followed by the careful slow addition of methanesulfonyl chloride (517 mL, 6.68 mol). After stirring at 23° C. for 20 h, the mixture was partially concentrated in vacuo at 55° C. Water (18 L) was added to the concentrate, and the resulting suspension was stirred at 23° C. for 2 h. The solid was filtered and was then washed with water (4 L) and air dried on the filter. The solid was suspended in absolute ethanol (9 L), stirred at 23° C. for 9 h, and was then filtered. The solid was washed with absolute ethanol (2×2 L), and was then further dried in vacuo at 50° C. to afford the desired product, 2-amino-5-methanesulfonylamino-benzenesulfonamide (1.45 kg, 5.48 mol, 86%), as a purple solid.

1. concentrationthe mixture was partially concentrated in vacuo at 55° C
2. additionWater (18 L) was added to the concentrate
3. stirringthe resulting suspension was stirred at 23° C. for 2 h
4. filtrationThe solid was filtered
5. washwas then washed with water (4 L) and air
6. customdried on the filter
7. stirringstirred at 23° C. for 9 h
8. filtrationwas then filtered
9. washThe solid was washed with absolute ethanol (2×2 L)
10. customwas then further dried in vacuo at 50° C.

ORD record

ord-0068ea6b773946dc90dc9d70d24c6fd6

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765741B2