Water → N-(4-nitrophenyl)methanesulfonamide

HRID 730490Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N+:6]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)([O-:8])=[O:7].N1C=CC=CC=1.O>C(#N)C>[N+:6]([C:9]1[CH:15]=[CH:14][C:12]([NH:13][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:11][CH:10]=1)([O-:8])=[O:7]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of methanesulfonylchloride (47.1 mL, 0.61 mol) in acetonitrile (160 mL) was added over 40 min to a solution of 4-nitroaniline (80.0 g, 0.58 mol) and pyridine (70.2 mL, 0.87 mol) in acetonitrile (400 mL) at 25° C. The mixture was stirred at 25° C. for 19 h, and then water (800 mL) was added. The resulting suspension was stirred at 25° C. for 30 min, and then was filtered through medium paper using a Büchner funnel. The collected solid was washed with water (2×150 mL) and air-dried overnight to afford the desired product, N-(4-nitro-phenyl)-methanesulfonamide (111.4 g, 0.52 mol, 89% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 3.17 (3H, s), 7.35 (2H, d, J=9.4 Hz), 8.20 (2H, d, J=9.1 Hz), 10.69 (1H, s).

Workup

stirringThe resulting suspension was stirred at 25° C. for 30 min
filtrationwas filtered through medium paper
washThe collected solid was washed with water (2×150 mL)
customair-dried overnight

Sources & evidence

ORD record: ord-82ff58ed73bf485b82ddbcc76c8f410c
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582754B2

Reaction notes

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