Hydrogen Peroxide → HCID 11226895, compound

HRID 1661921Notes

Reaction equation

HRID 1661921 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]=2[C:5]([O:24][CH3:25])=[CH:4][C:3]=1[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([CH3:35])=[O:34].OO.CC[O:40]C(C)=O>C(O)(=O)C>[Br:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH:17]([CH3:18])[CH3:19])=[CH:13][CH:12]=3)[N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]=2[C:5]([O:24][CH3:25])=[CH:4][C:3]=1[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([CH3:35])(=[O:40])=[O:34]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 11398805HCID 11398805, compound

Product 1

HCID 11226895HCID 11226895, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 140 mg (0.252 mmol) of 4-Bromo-2-(4-isopropyl-phenyl)-5-(2-methanesulfinyl-benzyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole and 30 μl (0.265 mmol) hydrogen peroxide solution (30%) in 3 ml acetic acid is stirred at reflux temperature for 3 h. After that the reaction mixture is allowed to cool to room temperature and 25 ml EtOAc are added and this solution is washed with 4n NaOH (2×), water and sodiumhydrogensulfite solution, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=1:1) to afford 112 mg of the title compound as pale red crystals.

Workup

  1. temperatureat reflux temperature for 3 h
  2. washthis solution is washed with 4n NaOH (2×), water and sodiumhydrogensulfite solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=1:1)

Sources & evidence

ORD record
ord-5f86c2fdc13d4b65a9b57ccc235a63f6
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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