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

HRID 1172379Notes

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 (11.16 g, 59.61 mmol) was dissolved in acetonitrile (300 mL) and pyridine (7.07 g, 89.41 mmol) was added. Methanesulfonyl chloride (7.17 g, 62.59 mmol) was added dropwise over a period of 10 min and the reaction mixture was stirred for 16 h at 25° C. after which time a precipitate had formed. Most of the acetonitrile was removed in vacuo and water (200 mL) was added to afford a clear solution. The product slowly started to precipitate and the mixture was placed in an ice bath for 3 h. The precipitate was collected by vacuum filtration and dried under high vacuum to afford the desired product, 2-amino-5-methanesulfonylamino-benzenesulfonamide (11.1 g, 41.84 mmol, 70.2% yield) as a brown 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 was removed in vacuo and water (200 mL)
additionwas added
customto afford a clear solution
customto precipitate
waitthe mixture was placed in an ice bath for 3 h
filtrationThe precipitate was collected by vacuum filtration
customdried under high vacuum

Sources & evidence

ORD record: ord-75edd83a348c47c0911749dba72f8ae2
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834009B2

Reaction notes

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