Ethylamine → 4-bromo-N-ethyl-3-fluorobenzenesulfonamide

HRID 2239444Notes

Reaction equation

HRID 2239444 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12].[CH2:13]([NH2:15])[CH3:14]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:15][CH2:13][CH3:14])(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 27782184-Bromo-3-fluorobenzenesulfonyl chloride

Product 1

HCID 684751604-bromo-N-ethyl-3-fluorobenzenesulfonamideYield 92.3%

Procedure

According to general procedure A, 4-Bromo-3-fluoro-benzenesulfonyl chloride (0.40 g, 1.46 mmol) and ethylamine (5 mL, 10.0 mmol, 2.0 M in THF) were stirred together for 16 hours. 4-bromo-N-ethyl-3-fluorobenzenesulfonamide (0.38 g, 92%) was provided after purification. HRMS: calcd for C8H9BrFNO2S, 280.95214; found (EI, M+.), 280.951. HPLC purity 100.0% at210-370 nm, 9.6 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-56d61e43c25a45f0ad1c42c5a8fa586d
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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