Dimethylamine → 4-bromo-N,N,3-trimethylbenzenesulfonamide

HRID 1644689Notes

Reaction equation

HRID 1644689 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][NH:11][CH3:12].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][C:15]=1[CH3:24]>O1CCCC1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([N:11]([CH3:12])[CH3:10])(=[O:22])=[O:21])=[CH:16][C:15]=1[CH3:24]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 27375034-Bromo-3-methylbenzene-1-sulfonyl chloride

Product 1

HCID 79380854-bromo-N,N,3-trimethylbenzenesulfonamideYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diisopropylethylamine (4.95 mL, 27.8 mmol) was added at 0° C. to a stirred solution of dimethylamine (3.70 mL, 55.6 mmol) in tetrahydrofuran (25 mL) and the reaction mixture was stirred at room temperature for 15 minutes. A 0.1 M solution of 4-bromo-3-methyl-benzenesulfonyl chloride (3.0 g, 11 mmol) in tetrahydrofuran was added at room temperature and the reaction mixture was stirred at room temperature for 2 hours. The solvent was evaporated off under reduced pressure. The residue was diluted with ethyl acetate, and the inorganic salts were filtered through a celite bed. The filtrate was washed with 2 N aqueous HCl, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford 2.90 g (94%) of 4-bromo-3-methyl-N,N-dimethyl-benzenesulfonamide, which was used in subsequent reactions without further purification. MS cald. for C9H12BrNO2S [M+] 278.2, obsd. 280.0.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 hours
  2. customThe solvent was evaporated off under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. filtrationthe inorganic salts were filtered through a celite bed
  5. washThe filtrate was washed with 2 N aqueous HCl
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f26fe62a1c044ba9eea78ef6aab2bcb
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

Loading…