Dichloromethane → 2-bromo-N-tert-butylbenzenesulfonamide

HRID 2421763Notes

Reaction equation

HRID 2421763 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].C(Cl)Cl.[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16].CCN(C(C)C)C(C)C>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:10])=[O:9]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 5204032-Bromobenzenesulfonyl chloride

Product 1

HCID 48250142-bromo-N-tert-butylbenzenesulfonamideYield 97.1%

Procedure

2-Bromobenzenesulfonyl chloride (100.9 g, 394.9 mmol) was dissolved in methylene chloride (500 mL, 8.0 mol) and cooled at 0° C. t-Butylamine (41.3 mL, 395 mmol) was added in 3 portions over approximately 1 minute. DIPEA (75.7 mL, 434 mmol) was immediately added in 3 portions over approximately 1 minute. The mixture was warmed to room temperature and stirred overnight. The product was washed with 1M H3PO4 (2×), with saturated. NaHCO3, and with saturated aqueous NaCl, then dried over MgSO4, filtered, and concentrated to yield 2-bromo-N-t-butyl-benzenesulfonamide (112 g) as a light brown solid.

Workup

  1. additionwas added in 3 portions over approximately 1 minute
  2. washThe product was washed with 1M H3PO4 (2×)
  3. dry with materialNaHCO3, and with saturated aqueous NaCl, then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-87461785402a42e99c45c6d1e90414c7
Source dataset
uspto-grants-2011_06
Patent number
US07956054B2

Reaction notes

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