Dimethylamine → 3-bromo-N,N-dimethylbenzenesulfonamide

HRID 2388945Notes

Reaction equation

HRID 2388945 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:12][NH:13][CH3:14].C1COCC1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([N:13]([CH3:14])[CH3:12])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 17943m-Bromobenzenesulphonyl chloride

Product 1

HCID 71298453-bromo-N,N-dimethylbenzenesulfonamideYield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into a 20 mL scintillation vial were added 3-Bromobenzenesulfonyl chloride (0.301 g, 1.179 mmol) and anhydrous pyridine (5 mL). A 2M solution of dimethylamine in THF (1.0 mL, 2.0 mmol) was added dropwise, and the reaction mixture was stirred at rt under N2 for 5 h after which it was concentrated under vacuum. The crude residue was partitioned between EtOAc and 1M citric acid. The layers were separated, and the organic phase was washed 3× with 1M citric acid, then treated with brine, dried (Na2SO4), filtered and concentrated. Trituration with Et2O provided 3-Bromo-N,N-dimethyl-benzenesulfonamide as a white powder (0.297 g, 96%). MS: m/z 263.9/265.9 [MH+].

Workup

  1. concentrationwas concentrated under vacuum
  2. customThe crude residue was partitioned between EtOAc and 1M citric acid
  3. customThe layers were separated
  4. washthe organic phase was washed 3× with 1M citric acid
  5. additiontreated with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b2d31b338d6b44e1a4d85f8b92497110
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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