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

HRID 1471226Notes

Reaction equation

HRID 1471226 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
  3. waitfor 16 hours
  4. customThe mixture was quenched slowly with 50 ml water
  5. extractionextracted twice with ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltration and solvent removal
  8. customthe product was purified by silica gel chromatography
  9. customA solid was obtained
  10. temperaturecooled
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-5ea8fce95a564d04b9b5aedb63103b20
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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