Benzimidazole → 2-(1H-Benzimidazol-1-yl)ethan-1-ol

HRID 1970679Notes

Reaction equation

HRID 1970679 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[O:10]1CC[CH2:12][CH2:11]1.[H-].[Na+].ICCO>CO.C(OCC)(=O)C>[N:1]1([CH2:12][CH2:11][OH:10])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 5798BenzimidazoleHCID 8028TetrahydrofuranHCID 12225IodoethanolHCID 24758Sodium hydride

Product 1

HCID 2281312-(1H-Benzimidazol-1-yl)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flask were added 2.3 g benzimidazole and 40 ml tetrahydrofuran and the mixture was cooled to 10 C under nitrogen. 1.0 g Sodium hydride were added in portions and the reaction mixture was stirred for 20 minutes. 4.0 g 2-Iodoethanol were added and the mixture was heated to 50 C for 16 hours. The mixture was quenched slowly with 50 ml water, extracted twice with ethyl acetate and dried over sodium sulfate. Following filtration and solvent removal, the product was purified by silica gel chromatography using 25% methanol in ethyl acetate. A solid was obtained that was dissolved in a hot mixture of 10% methanol in ethyl acetate, cooled, filtered and dried giving 1.4 g white solid.

Workup

  1. temperaturethe mixture was cooled to 10 C under nitrogen
  2. temperaturethe mixture was heated to 50 C for 16 hours
  3. customThe mixture was quenched slowly with 50 ml water
  4. extractionextracted twice with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltration and solvent removal
  7. customthe product was purified by silica gel chromatography
  8. customA solid was obtained
  9. temperaturecooled
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-42b294e169f24880959fe27aa6db60e3
Source dataset
uspto-grants-2013_04
Patent number
US08431045B2

Reaction notes

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