Sodium hydride → 2,3-dichloro-N-(2-fluoro-4-nitrophenyl)benzenesulfonamide

HRID 1361695Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH2:13].[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[S:22](Cl)(=[O:24])=[O:23]>C1COCC1>[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[S:22]([NH:13][C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[F:3])(=[O:24])=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To NaH (60% dispersion in mineral oil) (0.734, 18.3 mmol) in THF (100 mL) at 0° C. was added dropwise a solution of 2-fluoro-4-nitrobenzenamine (2.20 g, 14.1 mmol) in THF (25 mL). The solution turned deep red in color and was stirred at 0° C. for 1 hour. A solution of 2,3-dichlorobenzene-1-sulfonyl chloride (3.80 g, 15.5 mmol) in THF (25 mL) was then added dropwise, at which point the reaction turned orange/yellow in color. The mixture was allowed to warm to room temperature and then was stirred for and additional 30 minutes. The reaction was quenched by addition of NH4Cl (aq., sat.), and then concentrated. The mixture was partitioned between water and ethyl acetate. The organics were dried with MgSO4, filtered, and concentrated to afford 2,3-dichloro-N-(2-fluoro-4-nitrophenyl)benzenesulfonamide.

Workup

temperatureto warm to room temperature
stirringwas stirred for and additional 30 minutes
customThe reaction was quenched by addition of NH4Cl (aq., sat.)
concentrationconcentrated
customThe mixture was partitioned between water and ethyl acetate
dry with materialThe organics were dried with MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-f69687db22f14a82b4f820fab8cfcd14
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880000B2

Reaction notes

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