Methylamine → 4-bromo-N-methyl-2-(trifluoromethoxy)benzenesulfonamide

HRID 2239472Notes

Reaction equation

HRID 2239472 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([O:12][C:13]([F:16])([F:15])[F:14])[CH:3]=1.[CH3:17][NH2:18]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:18][CH3:17])(=[O:10])=[O:9])=[C:4]([O:12][C:13]([F:16])([F:15])[F:14])[CH:3]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 27364214-Bromo-2-(Trifluoromethoxy)Benzene-1-Sulfonyl Chloride

Product 1

HCID 594434404-bromo-N-methyl-2-(trifluoromethoxy)benzenesulfonamideYield 61%

Procedure

According to general procedure A, 4-Bromo-2-trifluoromethoxy-benzenesulfonyl chloride (0.35 g, 1.03 mmol) and methylamine (10 mL, 33% in ethanol) were stirred in sealed tube for 16 hours. 4-bromo-N-methyl-2-(trifluoromethoxy)benzenesulfonamide (0.21 g, 61%) was provided after purification. MS (ESI) m/z 334. HPLC purity 98.0% at 210-370 nm, 8.8 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-620da19be99a45638b1c3a01da76f8d8
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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