Hydrogen Peroxide → HCID 22285394, compound

HRID 1062451Notes

Reaction equation

HRID 1062451 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH:10]=[C:11]([C:13]([N:15]2[CH2:20][CH2:19][S:18][CH2:17][CH2:16]2)=[O:14])[N:12]=1.OO.C([O-])(O)=[O:31].[Na+]>CC(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH:10]=[C:11]([C:13]([N:15]2[CH2:16][CH2:17][S:18](=[O:31])[CH2:19][CH2:20]2)=[O:14])[N:12]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 22285567HCID 22285567, compound

Product 1

HCID 22285394HCID 22285394, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 4-{[2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl]carbonyl}thiomorpholine (Table entry 176) (30 mg, 0.072 mmol) in acetone (2 mL), was added 30% aqueous H2O2 (0.09 mmol). The resulting solution was stirred at rt for 36 h, diluted with water, neutralized with NaHCO3, and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (20% MeOH in EtOAc) to give the product 4-{[2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl]carbonyl}thiomorpholine 1-oxide (17 mg, 54% yield): LC-MS m/z 434.5 (MH+), retention time 2.55 min (method 1); Rf=0.47 (17% EtOAc in hexane).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (20% MeOH in EtOAc)

Sources & evidence

ORD record
ord-cd8a06cc4f1748d488c04413c1bcdcc9
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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