Hydrochloric Acid → Benzenesulfonamide, p-bromo-N-isobutyl-

HRID 1049004Notes

Reaction equation

HRID 1049004 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH2:18]([NH2:22])[CH:19]([CH3:21])[CH3:20].Cl>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:22][CH2:18][CH:19]([CH3:21])[CH3:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6558IsobutylamineHCID 7396p-Bromobenzenesulfonyl chloride

Product 1

HCID 101309Benzenesulfonamide, p-bromo-N-isobutyl-Yield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromobenzenesulfonyl chloride (2 g, 7.8 mmol) in DCM (40 mL) was added pyridine (1.9 mL, 23.5 mmol) followed by isobutylamine (1.56 mL, 15.7 mmol) and the reaction was stirred at room temperature for 16 hours. 1M aqueous HCl was added and the reaction extracted with DCM, filtered through a phase separator and concentrated to give 4-bromo-N-isobutyl-benzenesulfonamide (1.99 g). LCMS (m/z, Method A) ES+ 294[M+1]+

Workup

  1. extractionthe reaction extracted with DCM
  2. filtrationfiltered through a phase separator
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0271f673776a449892168f7c69951144
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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