Hydrochloric Acid → 2-bromo-N-tert-butylbenzenesulfonamide

HRID 257254

Reaction equation

HRID 257254 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:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13].Cl>C(Cl)Cl>[C:12]([NH:16][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])(=[O:10])=[O:9])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 5204032-Bromobenzenesulfonyl chloride

Product 1

HCID 48250142-bromo-N-tert-butylbenzenesulfonamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.0 g (16 mmol) 2-bromobenzenesulfonyl chloride in 75 mL methylene chloride at 0° C. was added 3.7 mL (35 mmol) tert-butylamine. The mixture was allowed to warm to RT and stir for 1 hour. The mixture was poured into aqueous 5% HCl and extracted three times with ether. The combined organic material was dried over MgSO4, was stripped of solvent in vacuo, then was recrystallized from hexane/acetone to give 3.19 g (70% yield) of the title compound. Rf 0.17 in 10% EtOAc/hexane, visualized by UV;

Workup

  1. extractionextracted three times with ether
  2. dry with materialThe combined organic material was dried over MgSO4
  3. customwas recrystallized from hexane/acetone

Sources & evidence

ORD record
ord-6c545eb3be8e47fd85a008b6d9b85be2
Source dataset
uspto-grants-1993_11
Patent number
US05260285

Linked notes

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