Benzimidazole → 1H-Benzimidazole, 1-methyl-

HRID 26699

Reaction equation

HRID 26699 reaction equation
[CH3:1]I.[OH-].[K+].[N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][CH:6]=1>C(O)C.O>[CH3:1][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1

Participants

6

Reactant 3

HCID 5798BenzimidazoleHCID 6328Methyl iodideHCID 14797Potassium Hydroxide

Product 1

HCID 958901H-Benzimidazole, 1-methyl-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

14.1 g of methyl iodide and 6.15 g of potassium hydroxide were added to a suspension of 11.8 g of benzimidazole in 50 ml of ethanol and 30 ml of water and the mixture was refluxed for 6 hours and was then cooled. The mixture was extracted three times with chloroform and the combined chloroform extracts were dried and filtered. The filtrate was evaporated to dryness and the oily residue was chromatographed over neutral alumina. Elution with chloroform yielded 1-methyl-benzimidazole as a crude oil which was used as is for the next step.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. temperaturewas then cooled
  3. extractionThe mixture was extracted three times with chloroform
  4. dry with materialthe combined chloroform extracts were dried
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe oily residue was chromatographed over neutral alumina
  8. washElution with chloroform

Sources & evidence

ORD record
ord-d0da4f3d7c0e4e4b8179c663b488848e
Source dataset
uspto-grants-1979_04
Patent number
US04151280

Linked notes

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