2-(Hydroxymethyl)-1H-benzimidazole → 1H-Benzimidazole-2-carboxaldehyde

HRID 976108Notes

Reaction equation

HRID 976108 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1>C(O)C.O=[Mn]=O>[N:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[NH:7][C:3]=1[CH:2]=[O:1]

Participants

4

Reactant 1

HCID 785692-(Hydroxymethyl)-1H-benzimidazole

Product 1

HCID 768261H-Benzimidazole-2-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-Hydroxymethyl-benzimidazole (11.9 g) and MnO2 (59.5 g) in ethanol (250 mL) was vigorously stirred for 2 days. The reaction was concentrated in vacuo, hot dimethylformamide was added and the mixture was filtered through celite. After removal of the solvent in vacuo the tan solid was triturated with ethanol to afford 2-Benzimidazolecarboxaldehyde as a tan powder.

Workup

  1. concentrationThe reaction was concentrated in vacuo, hot dimethylformamide
  2. additionwas added
  3. filtrationthe mixture was filtered through celite
  4. customAfter removal of the solvent in vacuo the tan solid
  5. customwas triturated with ethanol

Sources & evidence

ORD record
ord-e579fc5826294b658975003210e1457e
Source dataset
uspto-grants-1997_03
Patent number
US05610299

Reaction notes

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