Water → 1-Ethyl-1H-benzimidazole

HRID 1471209Notes

Reaction equation

HRID 1471209 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[OH-].[Na+].O.S(OCC)(O[CH2:17][CH3:18])(=O)=O>O1CCCC1>[CH2:17]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1)[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 5798BenzimidazoleHCID 6163Diethyl SulfateHCID 14798Sodium Hydroxide

Product 1

HCID 4850941-Ethyl-1H-benzimidazoleYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flask were added 100 g benzimidazole, 44 g sodium hydroxide, 320 ml water and 480 ml tetrahydrofuran and the mixture was stirred under nitrogen. 157 g Diethyl sulfate were added slowly, maintaining a temperature of 40 C. After 2 hrs at 40 C, the reaction was quenched with slow addition of 100 ml concentrated hydrochloric acid. After washing with 150 ml hexane, the mixture was basified with 50 g sodium hydroxide and extracted with 275 ml ethyl acetate, then 225 ml ethyl acetate. The solvent was removed, leaving an orange oil, which was distilled under full vacuum to give 109.4 g clear colorless oil.

Workup

  1. customthe reaction was quenched with slow addition of 100 ml concentrated hydrochloric acid
  2. washAfter washing with 150 ml hexane
  3. extractionextracted with 275 ml ethyl acetate
  4. customThe solvent was removed
  5. customleaving an orange oil, which
  6. distillationwas distilled under full vacuum

Sources & evidence

ORD record
ord-77bd235278484fb88579be3072e872f1
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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