4-Fluorobenzenesulfonyl chloride → 4-fluoro-N,N-dimethylbenzenesulfonamide

HRID 238586Notes

Reaction equation

HRID 238586 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.Cl.[CH3:13][NH:14][CH3:15]>O1CCCC1.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:14]([CH3:15])[CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 7993014-fluoro-N,N-dimethylbenzenesulfonamideYield 50.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-fluorobenzenesulfonyl chloride (1.95 g, 10 mmol) and dimethylamine hydrochloric acid salt (978 mg, 12 mmol) in tetrahydrofuran (10 mL) was added to a solution of 4-dimethylaminopyridine (3.05 g, 25 mmol) in tetrahydrofuran (10 mL) dropwise at room temperature. The resulting mixture was stirred at room temperature overnight and concentrated in vacuo. The residue was purified by flash column (elution with 20% ethyl acetate in petroleum ether) to afford 4-fluoro-N,N-dimethyl-benzenesulfonamide (1.02 g, 50%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column (elution with 20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-c34f281a33e1453d9f9dfb56f45d63b8
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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