Isobutylamine → Benzenesulfonamide, p-bromo-N-isobutyl-

HRID 2239391Notes

Reaction equation

HRID 2239391 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.[CH2:12]([NH2:16])[CH:13]([CH3:15])[CH3:14]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:16][CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 7396p-Bromobenzenesulfonyl chloride

Product 1

HCID 101309Benzenesulfonamide, p-bromo-N-isobutyl-Yield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to general procedure C, 4-Bromobenzene sulfonyl chloride (0.40 g, 1.56 mmol) and isobutylamine (0.39 mL, 3.90 mmol) were stirred together with dry dichloromethane (5 mL) for 16 hours. 4-bromo-N-isobutylbenzenesulfonamide (0.12 g, 28%) was provided after purification. MS (ESI) m/z 292.HPLC purity 100.0% at 210-370 nm, 9.4 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

Sources & evidence

ORD record
ord-465d42e183414a8bae96ff329c7f9934
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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