Hydrogen Peroxide → 5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

HRID 1627311Notes

Reaction equation

HRID 1627311 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:15](S)=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].OO.[OH-].[Na+]>C(Cl)Cl.CC(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[CH:15]=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 178439130HCID 178439130, compound

Product 1

HCID 667399875-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazoleYield 69%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol (737 mg, 1.9 mmol) in DCM (4 mL) at 0° C. was added a solution of 0.6 mL H2O2 (35% wt.) in HOAc (2 mL). After stirring 40 min, the mixture was allowed to warm to room temperature. After stirring 6 h, the reaction mixture was neutralized to pH 9 using 2N NaOH and was extracted with DCM. The combined extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. The crude material was purified by chromatography (silica, 0-95% EtOAc/Hex) to give 5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole as a white solid (455 mg, 69% yield).

Workup

  1. stirringAfter stirring 6 h
  2. extractionwas extracted with DCM
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by chromatography (silica, 0-95% EtOAc/Hex)

Sources & evidence

ORD record
ord-0e31a5cdcd1d4929b0d0243ca0def118
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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