Tert-Butylamine → N-t-Butyl 4-bromobenzenesulfonamide

HRID 2239397Notes

Reaction equation

HRID 2239397 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.[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:16][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 7396p-Bromobenzenesulfonyl chloride

Product 1

HCID 796629N-t-Butyl 4-bromobenzenesulfonamideYield 26.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to general procedure C, 4-Bromobenzene sulfonyl chloride (0.40 g, 1.56 mmol) and tert-butylamine (0.41 mL, 3.90 mmol) were stirred together in dry dichloromethane (5 mL) for 16 hours. 4-bromo-N-(tert-butyl)benzenesulfonamide (0.12 g) was provided after purification. MS (ESI) m/z 292. HPLC purity 100.0% at 210-370 nm, 9.2 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-e0249425b56843a484f3eceb45158d87
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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