Tert-Butylamine → 3-Bromo-N-tert-butylbenzene-1-sulfonamide

HRID 1622113Notes

Reaction equation

HRID 1622113 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:13][C:14]1[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1>ClCCl>[C:1]([NH:5][S:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([Br:13])[CH:15]=1)(=[O:22])=[O:21])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 17943m-Bromobenzenesulphonyl chloride

Product 1

HCID 48209263-Bromo-N-tert-butylbenzene-1-sulfonamideYield 1,248%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butylamine (3.14 g, 3.0 mmol, 1.1 eq) and triethylamine (5.94 g, 58.6 mmol, 1.5 eq.) were dissolved in dichloromethane (20 mL) and stirred at room temperature while 3-bromobenzenesulfonyl chloride (10.0 g, 39.1 mmol) was added slowly. The mixture was stirred for 1 hour and then concentrated by evaporation under reduced pressure. The residue was taken up in 5% citric acid and ethyl acetate. The organic layer is washed repeatedly with brine and water, dried over anhydrous magnesium sulfate and concentrated to give N-tert-butyl-3-bromobenzenesulfonamide (10.94 g) as a white powder.

Workup

  1. additionwas added slowly
  2. concentrationconcentrated by evaporation under reduced pressure
  3. washThe organic layer is washed repeatedly with brine and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c612875de97e466087f8d1e095fb1884
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

Loading…