Sodium Iodide → N-(5-Acetyl-2-benzyloxyphenyl)-N-benzylmethanesulfonamide

HRID 1696839Notes

Reaction equation

HRID 1696839 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7](O)=[C:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=1)(=[O:3])[CH3:2].[I-].[Na+].[C:18](=[O:21])([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(C)=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:21][CH2:18][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[C:8]([N:10]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 19073226N-(5-acetyl-2-hydroxyphenyl)methanesulfonamide

Product 1

HCID 12363924N-(5-Acetyl-2-benzyloxyphenyl)-N-benzylmethanesulfonamideYield 199.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-(5-acetyl-2-hydroxyphenyl)methanesulfonamide (31) (0.30 g, 1.32 mmol), sodium iodide (0.20 g, 1.32 mmol), potassium carbonate (0.91 g, 6.58 mmol), and benzyl bromide (0.39 mL, 3.28 mmol) in acetone (10 mL) was stirred under reflux for 66 h. After removal of solvent by rotary evaporation, the resulting residue was diluted with dichloromethane and insoluble inorganics were vacuum filtered. The filtrate was concentrated in vacuo and the resulting residue was purified by flash silica gel column chromatography eluting with a mixture of ethyl acetate (0-3%) in dichloromethane to give benzyl ether 32 as a yellow solid (0.54 g, 99%): 1H NMR (300 MHz, CDCl3) δ 2.38 (s, 3H), 2.85 (s, 3H), 4.75 (br, 2H), 5.18 (s, 2H), 7.05 (d, 1H), 7.23 (m, 5H), 7.42 (m, 5H), 7.62 (d, 1H), 7.89 (dd, 1H); m/z (ESI) 410 [C23H23NO4S+H]+.

Workup

  1. temperatureunder reflux for 66 h
  2. customAfter removal of solvent
  3. customby rotary evaporation
  4. additionthe resulting residue was diluted with dichloromethane and insoluble inorganics
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe resulting residue was purified by flash silica gel column chromatography
  8. washeluting with a mixture of ethyl acetate (0-3%) in dichloromethane

Sources & evidence

ORD record
ord-79ef7aed58804b88b0576686bc7e6a6a
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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