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

HRID 1278735Notes

Reaction equation

HRID 1278735 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-6598c9dfe1654bb79b0b96437880a533
Source dataset
uspto-grants-2002_09
Patent number
US06444685B1

Reaction notes

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