4-Fluorobenzenesulfonyl chloride → N-(3,4-dimethoxyphenyl)-4-fluorobenzenesulfonamide

HRID 351678Notes

Reaction equation

HRID 351678 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][S:19]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 227703,4-Dimethoxyaniline

Product 1

HCID 741636N-(3,4-dimethoxyphenyl)-4-fluorobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,4-Dimethoxyaniline(1.01 g, 6.99 mM) was added to a solution of 4-Fluorobenzenesulfonyl chloride (1.50 g, 7.69 mM) in anhydrous pyridine(10 ml). The reaction was stirred overnight. The reaction was quenched with 1N HClaq.(20 ml) and washed with ethyl acetate(3×20 ml). The organic extracts were combined, dried(sodium sulfate), solids filtered off and concentrated. The desired product was isolated using silica gel flash chromatography of 1.30 g as a yellow solid. H1 NMR(CDCl3) δ 3.79(s, 3H), 3.86(s, 3H), 6.50(d, 1H, J=4.71 Hz), 6.68(d, 1H, J=2.64 Hz), 6.71(d, 1H, J=2.76 Hz), 7.11(d, 2H, J=8.67 Hz), 7.75(m, 2H). MS(ES) m/z 328.9; (M+NH4+); HRMS for (MH+) C14H14SFNO4: 260.1511.

Workup

  1. customThe reaction was quenched with 1N HClaq
  2. wash(20 ml) and washed with ethyl acetate(3×20 ml)
  3. filtrationdried(sodium sulfate), solids filtered off
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f0ea76f8fac8450d88bb327eb9f2a4ba
Source dataset
uspto-grants-2004_06
Patent number
US06743787B2

Reaction notes

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