Dimethylamine → 4-Bromo-N,N-dimethylbenzenesulphonamide

HRID 2258345Notes

Reaction equation

HRID 2258345 reaction equation
[CH3:1][NH:2][CH3:3].[Br:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1>O1CCCC1.C(OCC)C>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:2]([CH3:3])[CH3:1])(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 7396p-Bromobenzenesulfonyl chloride

Product 1

HCID 128184-Bromo-N,N-dimethylbenzenesulphonamideYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 25% aqueous solution of dimethylamine (420 mL, 2.3 mol) was diluted with 1000 mL of tetrahydrofuran and added dropwise to a solution of p-bromobenzenesulfonyl chloride (200 g, 0.78 mol) in 700 mL of tetrahydrofuran. The mixture was diluted with diethyl ether and the organic layer was washed with water and saturated aqueous sodium chloride and dried over sodium sulfate. Evaporation of the solvent gave 195.4 g (95%) of 4-bromo-N,N-dimethylbenzenesulfonamide as white crystals, mp 90°-92° C. (lit. 94° C., J. Am. Chem. Soc. 45, 2696 (1923)).

Workup

  1. washthe organic layer was washed with water and saturated aqueous sodium chloride
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-9140cd2c6f59401e9c9d39f4dd59d4d2
Source dataset
uspto-grants-1997_08
Patent number
US05658908

Reaction notes

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