[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-yl]-methanol → 1-(3,5-dichloro-benzyl)-1H-imidazole-2-carbaldehyde

HRID 2101484Notes

Reaction equation

HRID 2101484 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][OH:12]>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH:11]=[O:12]

Participants

4

Reactant 1

HCID 57801498[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-yl]-methanol

Product 1

HCID 578014901-(3,5-dichloro-benzyl)-1H-imidazole-2-carbaldehydeYield 90%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of [1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-methanol (see Example 1) (2.02 g, 7.88 mmol) in CH2Cl2 (10 mL) at ambient temperature was added MnO2 (6.78 g, 78.0 mmol). The mixture was stirred for 5 h then filtered through a diatomaceous earth pad. Removal of the solvent in vacuo provided 1-(3,5-dichloro-benzyl)-1H-imidazole-2-carbaldehyde (1.80 g, 90%) as a white solid: ESI MS m/z 225 [C11H8Cl2N2O+H]+.

Workup

  1. filtrationthen filtered through a diatomaceous earth pad
  2. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-fc678b3372464995a3a71509e89d94e9
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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