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

HRID 731227Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].N1C=CC=CC=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(#N)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:10])=[O:11]

Participants

Conditions

Temperature: 25 °C

Procedure

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+].

Workup

customhad formed
customMost of the acetonitrile (approximately 110 mL) was removed in vacuo and water (120 mL)
additionwas added
customto afford a clear solution
customA purple solid precipitated from this solution over the next 2 h
filtrationThis precipitate was collected by vacuum filtration
washwashed with methyl-tert-butyl ether (3×30 mL)
customdried in vacuo overnight at 50° C.

Sources & evidence

ORD record: ord-036793ef84ac4dcd9bee770f5559b801
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582626B2

Reaction notes

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