Pyridine → 4-Fluoro-N-(4-fluorophenyl)benzenesulfonamide

HRID 1049008Notes

Reaction equation

HRID 1049008 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:23][C:22]2[CH:24]=[CH:25][C:19]([F:18])=[CH:20][CH:21]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 97314-Fluoroaniline

Product 1

HCID 5735404-Fluoro-N-(4-fluorophenyl)benzenesulfonamideYield 78%

Procedure

To a solution of 4-fluorobenzenesulfonyl chloride (2 g, 10.3 mmol) at room temperature was stirred with pyridine (2.49 mL, 30.8 mmol) and 4-fluoroaniline (1.95 mL, 20.6 mmol) for 2 hrs. The reaction was quenched with 1 M HCl aqueous and then extracted with DCM, filtered through a phase separator and purified by silica gel column chromatography (0-100% DCM in cyclohexane) to give 4-fluoro-N-(4-fluoro-phenyl)-benzenesulfonamide (2.15 g, 78%). LCMS (m/z, Method A) ES+ 270 [M+1]+.

Workup

  1. customThe reaction was quenched with 1 M HCl aqueous
  2. extractionextracted with DCM
  3. filtrationfiltered through a phase separator
  4. custompurified by silica gel column chromatography (0-100% DCM in cyclohexane)

Sources & evidence

ORD record
ord-674833a7699a48f6b10cb3365ed42dd9
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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