4-Nitrobenzenesulfonyl chloride → N-[2-(2,4-dichlorophenoxy)phenyl]-4-nitrobenzenesulfonamide

HRID 746743Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[Cl:15][C:16]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:17]=1[O:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21]>N1C=CC=CC=1>[Cl:15][C:16]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:17]=1[O:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH:21][S:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-nitrobenzenesulfonyl chloride (2.71 g, 12 mmol) and 2-(2,4-dichloro-phenoxy)aniline HCl (2.9 g, 10 mmol) were dissolved in pyridine (10 mL) at room temperature. After 1 hr the mixture was heated at 60° C. for 2 hour. The reaction mixture was concentrated under vacuum. The residue was diluted with EtOAc and washed sequentially with 1M aq. HCl and sat. aq. NaHCO3 and the organic extract dried over MgSO4, and the solvent removed in vacuo to afford the title compound as a solid. LCMS (ES MS, M+H+found: 439) and proton NMR (400 MHz, CDCl3) δ 6.54-6.62 (m, 2H), 7.02-7.18 (m, 4H), 7.43 (d, J=2.5 Hz, 1H), 7.73 (dd, J=8.1 and 1.6 Hz, 1H), 7.94 (d, J=8.6 Hz, 2H), 8.21 (d, J=8.6 Hz, 2H).

Workup

concentrationThe reaction mixture was concentrated under vacuum
additionThe residue was diluted with EtOAc
washwashed sequentially with 1M aq. HCl and sat. aq. NaHCO3
extractionthe organic extract
dry with materialdried over MgSO4
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-cd62f01374ec445f861d438515d65f47
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07393873B2

Reaction notes

Loading…