Formic Acid → 6-Methoxy-7-methyl-1H-benzimidazole

HRID 327450Notes

Reaction equation

HRID 327450 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:11])=[C:5]([NH2:10])[C:6]([NH2:9])=[CH:7][CH:8]=1.[CH:12](O)=O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[NH:9][CH:12]=[N:10][C:5]=2[C:4]=1[CH3:11]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 59245497433-22-2

Product 1

HCID 199193886-Methoxy-7-methyl-1H-benzimidazoleYield 84%

Conditions

Temperature
60 °C

Procedure

A mixture of 4-methoxy-3-methyl-1,2-benzenediamine (2.8 g, 18.4 mmol) and formic acid (30 mL) was heated at 60° C. for 30 minutes. The formic acid was removed under pressure and the product was partitioned between chloroform and water containing sufficient sodium hydroxide to basify the solution. After evaporation of the solvent the crude product was chromatographed (methanol:chloroform) to give 2.55 g (84%) of 5-methoxy-4-methyl-1H-benzimidazole.

Workup

  1. customThe formic acid was removed under pressure
  2. customthe product was partitioned between chloroform and water containing sufficient sodium hydroxide
  3. customAfter evaporation of the solvent the crude product
  4. customwas chromatographed (methanol:chloroform)

Sources & evidence

ORD record
ord-fc36aca38dfe4222af2349fc7f21e98b
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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