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

HRID 623360Notes

Reaction equation

HRID 623360 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-3139a3af72464d2f9ac8c1a9b4f2e56c
Source dataset
uspto-grants-2016_04
Patent number
US09302985B2

Reaction notes

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