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

HRID 1600340Notes

Reaction equation

HRID 1600340 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 wasfiltered 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. customAfter removal of the solvent in vacuo the tan solid
  4. customwas triturated with ethanol

Sources & evidence

ORD record
ord-577612f0378c4d57814c0c1dd2f0cc6e
Source dataset
uspto-grants-1998_04
Patent number
US05744603

Reaction notes

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