Selenium Dioxide → 1-Cyclopropyl-1H-benzimidazole-2-carbaldehyde

HRID 2231244Notes

Reaction equation

HRID 2231244 reaction equation
[Se](=O)=[O:2].[CH:4]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH3:16])[CH2:6][CH2:5]1>O1CCOCC1>[CH:4]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH:16]=[O:2])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 212862831-Cyclopropyl-2-methyl-1H-benzimidazole

Product 1

HCID 150720581-Cyclopropyl-1H-benzimidazole-2-carbaldehydeYield 57.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Selenium dioxide (1.2 g, 0.011 mole) was added to 60 ml of dioxane containing 1.87 g .(0.011 mole) of 1-cyclopropyl-2-methylbenzimidazole and the reaction heated to reflux for 2.5 hours. The reaction was filtered and the filtrate concentrated to a dark oil, 3.0 g. Chromatographing of the residue on silica gel gave 1.18 g of the desired compound.

Workup

  1. temperatureto reflux for 2.5 hours
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate concentrated to a dark oil, 3.0 g

Sources & evidence

ORD record
ord-e0ecb81061674e09bdf6a889217e79f0
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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