Triethylamine → 3-bromo-N,N-dimethylbenzenesulfonamide

HRID 2389285Notes

Reaction equation

HRID 2389285 reaction equation
Cl.[CH3:2][NH:3][CH3:4].C(N(CC)CC)C.[Br:12][C:13]1[CH:14]=[C:15]([S:19](Cl)(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])O.[Na+]>C1COCC1>[Br:12][C:13]1[CH:14]=[C:15]([S:19]([N:3]([CH3:4])[CH3:2])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 17943m-Bromobenzenesulphonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 71298453-bromo-N,N-dimethylbenzenesulfonamideYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In THF (10 mL), dimethylamine hydrochloride (2.04 g, 25.0 mmol) and triethylamine (3.48 mL, 25.0 mmol) were dissolved, and 3-bromobenzenesulfonyl chloride (0.721 mL, 5.00 mmol) was added thereto at 0° C., and then, the mixture was stirred at room temperature for 1 hour. To the mixture, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give 3-bromo-N,N-dimethylbenzenesulfonamide (1.23 g, 4.66 mmol, yield: 93%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cd0ecf020d9344888d8477b3a07a75da
Source dataset
uspto-grants-2012_09
Patent number
US08273738B2

Reaction notes

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