N-bromobutanimide → 4-amino-3-bromo-N-tert-butyl-benzenesulfonamide

HRID 1711293

Reaction equation

HRID 1711293 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1C(=O)N([Br:23])C(=O)C1>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])=[CH:4][C:3]=1[Br:23]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 8326274-Amino-N-(1,1-dimethylethyl)benzenesulfonamide

Product 1

HCID 548502844-amino-3-bromo-N-tert-butyl-benzenesulfonamideYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-N-tert-butyl-benzenesulfonamide (J. Med. Chem. (2003), 46(16), 3463-3475, 228 mg, 1.00 mmol) in DCM (10 mL), NBS (178 mg, 1.00 mmol) was added. The resulting mixture was stirred at RT for 30 min and washed with satd NaHCO3 (10 mL) and 10% aq Na2S2O3 (10 mL). The organic layer was separated, dried and concentrated to obtain 4-amino-3-bromo-N-tert-butyl-benzenesulfonamide (163 mg, 53%).

Workup

  1. washwashed with satd NaHCO3 (10 mL) and 10% aq Na2S2O3 (10 mL)
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-82168f1fbbe246799a59bd1f0f3f1298
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Linked notes

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