Acetic Acid → 2-Methylbenzimidazole

HRID 277694Notes

Reaction equation

HRID 277694 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[OH-].[K+].[C:11](O)(=O)[CH3:12]>>[CH3:11][C:12]1[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7243O-PhenylenediamineHCID 14797Potassium Hydroxide

Product 1

HCID 119842-MethylbenzimidazoleYield 77%

Procedure

Phenylene diamine (32 grams) and glacial acetic acid (60 ml) were refluxed for 2 hours. Ice and KOH were added to bring the pH to 8.0, and the resulting light violet solid was filtered and collected. Recrystallization from benzene yielded 30 grams of 2-methyl benzimidazole as a light yellow solid having a melting point of 170° C. and total yield of 77%.

Workup

  1. filtrationthe resulting light violet solid was filtered
  2. customcollected
  3. customRecrystallization from benzene

Sources & evidence

ORD record
ord-f662b28ea364484e9f360e8e760b0282
Source dataset
uspto-grants-2002_03
Patent number
US06358954B1

Reaction notes

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