Cyclopropanemethanamine → Benzenesulfonamide, 4-bromo-N-(cyclopropylmethyl)-2,5-difluoro-

HRID 2239500Notes

Reaction equation

HRID 2239500 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([S:9](Cl)(=[O:11])=[O:10])=[C:4]([F:13])[CH:3]=1.[CH:14]1([CH2:17][NH2:18])[CH2:16][CH2:15]1>ClCCl>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([S:9]([NH:18][CH2:17][CH:14]2[CH2:16][CH2:15]2)(=[O:11])=[O:10])=[C:4]([F:13])[CH:3]=1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 5745904-Bromo-2,5-difluorobenzenesulfonyl Chloride

Product 1

HCID 68482433Benzenesulfonamide, 4-bromo-N-(cyclopropylmethyl)-2,5-difluoro-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to general procedure C, 4-Bromo-2,5-difluorobenzenesulfonyl chloride (0.20 g, 0.68 mmol) and cyclopropylmethylamine were stirred together in dichloromethane (1 mL) for 16 hours. The reaction afforded 4-bromo-N-(cyclopropylmethyl)-2,5-difluorobenzenesulfonamide (0.17 g) after purification. HPLC purity 95.0% 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. HRMS: calcd for C10H10BrF2NO2S−H+, 323.95109; found (ESI-FTMS, [M−H]1−), 323.95103

Sources & evidence

ORD record
ord-1486b0ce18a8444abab57fdd9f14c45d
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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