Benzyl Bromide → N-Benzyl-N-(3,4-dimethoxy-phenyl)-4-fluoro-benzenesulfonamide

HRID 351679Notes

Reaction equation

HRID 351679 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:22]([N:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[S:12]([C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)(=[O:14])=[O:13])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 741636N-(3,4-dimethoxyphenyl)-4-fluorobenzenesulfonamide

Product 1

HCID 12051199N-Benzyl-N-(3,4-dimethoxy-phenyl)-4-fluoro-benzenesulfonamideYield 79.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(3,4-Dimethoxy-phenyl)-4-fluoro-benzenesulfonamide (0.51 g, 1.61 mM) was added to a solution of benzyl bromide (0.57 g, 4.82 mM) and potassium carbonate (0.66 g, 4.82 mM)in anhyrous acetone(10 ml). The reaction was stirred overnight. The undissolved solids were removed by filtration and the mother liquor was concentrated. This gum was triturated with hexanes to afford 0.52 g of the desired product as an off-white solid. H1 NMR(CDCl3) δ 3.66(s, 3H), 3.81(s, 3H), 6.42(m, 2H), 6.66(d, 1H, J=8.70 Hz), 7.23(m, 7H), 7.71(m, 2H). MS(ES) m/z 401.9; (MH+); HRMS for C21H20SFNO4: 401.1094.

Workup

  1. customThe undissolved solids were removed by filtration
  2. concentrationthe mother liquor was concentrated
  3. customThis gum was triturated with hexanes

Sources & evidence

ORD record
ord-bd562a81dfc94262b2a009f77b52b428
Source dataset
uspto-grants-2004_06
Patent number
US06743787B2

Reaction notes

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