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

HRID 2069933Notes

Reaction equation

HRID 2069933 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-be4121b5afbb485d8b946f7e9f3b281b
Source dataset
uspto-grants-2012_10
Patent number
US08299110B2

Reaction notes

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