Dimethylamine → Benzenesulfonamide, 4-bromo-N,N-dimethyl-2-(trifluoromethyl)-

HRID 2239418Notes

Reaction equation

HRID 2239418 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[CH3:16][NH:17][CH3:18]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:17]([CH3:18])[CH3:16])(=[O:10])=[O:9])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 27786084-Bromo-2-(trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 68410001Benzenesulfonamide, 4-bromo-N,N-dimethyl-2-(trifluoromethyl)-Yield 80%

Procedure

In an analogous manner to General Procedure A, 4-Bromo-2-trifluoromethylbenzenesulfonyl chloride (0.50 g, 1.54 mmol) and dimethylamine (10 mL, 33% in ethanol) were stirred in sealed tube for 16 hours. 4-bromo-N,N-dimethyl-2-(trifluoromethyl)benzenesulfonamide (0.41 g, 80%) was provided after purification. MS (ESI) m/z 332. HPLC purity 100.0% at 210-370 nm, 9.3 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-742413601bd94ec99eee5bb47ef06e14
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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