Hydrogen Peroxide → HCID 57772021, compound

HRID 1661920Notes

Reaction equation

HRID 1661920 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:32][CH3:33])=[CH:20][C:21]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[S:30][CH3:31])=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].OO.CC[O:38]C(C)=O>C(O)(=O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:32][CH3:33])=[CH:20][C:21]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[S:30]([CH3:31])=[O:38])=[CH:22][C:12]=3[N:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 57772063HCID 57772063, compound

Product 1

HCID 57772021HCID 57772021, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 714 mg (1.32 mmol) of 2-(4-Isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-5-(2-methylsulfanyl-benzyl)-1H-benzoimidazole and 142 μl (1.39 mmol) hydrogen peroxide solution (30%) in 13 ml acetic acid is stirred at room temperature for 1.5 h. After that 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 (EtOAc) to afford 496 mg of the title compound as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-8b005f6e3a464d83bef6ee93992021ba
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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