Cyclopropanemethanamine → 4-Bromo-N-(cyclopropylmethyl)-2-fluorobenzenesulfonamide

HRID 2239466Notes

Reaction equation

HRID 2239466 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([F:12])[CH:3]=1.[CH:13]1([CH2:16][NH2:17])[CH2:15][CH2:14]1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:17][CH2:16][CH:13]2[CH2:15][CH2:14]2)(=[O:10])=[O:9])=[C:4]([F:12])[CH:3]=1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 27363104-Bromo-2-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 684832004-Bromo-N-(cyclopropylmethyl)-2-fluorobenzenesulfonamideYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to general procedure C, 4-Bromo-2-fluoro-benzenesulfonyl chloride (0.40 g, 1.46 mmol) and cyclopropylmethylamine (0.31 mL, 3.65 mmol) were stirred together with dry dichloromethane (5 mL) for 16 hours. 4-bromo-N-(cyclopropylmethyl)-2-fluorobenzenesulfonamide (0.18 g, 40%) was provided after purification. MS (ESI) m/z 308. HPLC purity 97.7% at 210-370 nm, 10.7 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (Ammonium Bicarb Buff. pH=9.5/ACN+MeOH) for 10 min., hold 4 min.

Sources & evidence

ORD record
ord-765191e9b42f48a29acaeaa143101ab9
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

Loading…