Pyridine → 4-fluoro-N-{4-fluoro-3-nitrophenyl}benzenesulfonamide

HRID 15526Notes

Reaction equation

HRID 15526 reaction equation
N1C=CC=CC=1.[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16].[F:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>ClCCl>[F:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([F:7])=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 7989284-fluoro-N-{4-fluoro-3-nitrophenyl}benzenesulfonamideYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (500 uL, 6.19 mmol) was added to a solution of 4-fluoro-3-nitro-phenylamine (1 g, 6.41 mmol) and 4-fluoro-benzenesulfonyl chloride (1.2 g, 6.19 mmol) in dichloromethane (DCM) (20 mL) and the reaction was stirred at room temperature overnight. The reaction was then partitioned between water and DCM. The organic layer was washed several times with water and concentrated. Recrystalization from ethanol/water gave 1.57 g of the sub-title compound as tan crystals.

Workup

  1. customThe reaction was then partitioned between water and DCM
  2. washThe organic layer was washed several times with water
  3. concentrationconcentrated
  4. customRecrystalization from ethanol/water

Sources & evidence

ORD record
ord-6f17df37e00a4352aac9ba84d1fdc378
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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