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

HRID 1752885Notes

Reaction equation

HRID 1752885 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-f24f1bb07fe44da88800c85cb0d62889
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

Loading…