Dimethylamine → 4-Bromo-N,N-dimethylbenzenesulphonamide

HRID 732792Notes

Reaction equation

HRID 732792 reaction equation
[CH3:1][NH:2][CH3:3].C(N(CC)CC)C.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>C1COCC1.ClCCl.C(OCC)(=O)C>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:2]([CH3:3])[CH3:1])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 674DimethylamineHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 128184-Bromo-N,N-dimethylbenzenesulphonamideYield 97%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent3×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Place dimethylamine (5.25 mL of a 2.0 M solution in THF, 10.4 mmol), triethylamine (2.04 mL, 14.68 mmol) and dichloromethane (30 mL) in a round bottom flask. Cool this solution to 0° C., while stirring, and add a solution of 4-bromobenzenesulfonyl chloride (2.5 g, 9.78 mmol) in dichloromethane (30 mL). Add additional dichloromethane (10 mL) and stir the reaction overnight, letting it warm to ambient temperature. Concentrate the reaction in vacuo. Take up the resulting solid in ethyl acetate and filter. Evaporate the filtrate in vacuo and dry the resulting solid by vacuum to give 2.50 g of 4-bromo-N,N-dimethyl-benzenesulfonamide (97%).

Workup

  1. stirringstir
  2. customthe reaction overnight
  3. temperaturewarm to ambient temperature
  4. concentrationConcentrate
  5. customthe reaction in vacuo
  6. filtrationfilter
  7. customEvaporate the filtrate in vacuo
  8. customdry the resulting solid by vacuum

Sources & evidence

ORD record
ord-1ea77e5fd7f3460f9286e4d6dd573ee4
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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