Dimethylamine → 4-fluoro-N,N-dimethylbenzenesulfonamide

HRID 2390215Notes

Reaction equation

HRID 2390215 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.[CH3:12][NH:13][CH3:14]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:13]([CH3:14])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 95884-Fluorobenzenesulfonyl chloride

Product 1

HCID 7993014-fluoro-N,N-dimethylbenzenesulfonamideYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) solution of 4-fluorobenzenesulfonyl chloride (2.00 g; 10.3 mmol) in THF (40 ml) is treated with a 2 M solution of dimethylamine in THF (11.3 ml; 22.6 mmol) and stirred at 0° C. for 30 minutes. The solvents were removed under reduced pressure, the residue taken up in EtOAc, the organic phase was washed with a saturated solution of NH4Cl twice and with water. The organic phase was dried on MgSO4, filtered and the solvent removed under reduced pressure to afford the title compound (1.80 g, 86%).

Workup

  1. customThe solvents were removed under reduced pressure
  2. washthe organic phase was washed with a saturated solution of NH4Cl twice
  3. customThe organic phase was dried on MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-3045e8c60bf34aa7b9042b60e300d800
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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