Water → 2-[(1-methyl-1H-benzimidazol-2-yl)oxy]ethanol

HRID 333746Notes

Reaction equation

HRID 333746 reaction equation
[Na].[CH:2]([OH:5])(O)[CH3:3].Cl[C:7]1[N:11]([CH3:12])[C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[N:8]=1.[OH2:17]>>[CH3:12][N:11]1[C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[N:8]=[C:7]1[O:17][CH2:3][CH2:2][OH:5]

Participants

5

Reactant 4

HCID 962WaterHCID 1512111,1-EthanediolHCID 6630802-chloro-1-methyl-1H-1,3-benzodiazoleHCID 5360545Sodium

Product 1

HCID 895868382-[(1-methyl-1H-benzimidazol-2-yl)oxy]ethanol

Conditions

Temperature
60 °C

Procedure

Under an argon atmosphere, metal sodium (635 mg) was added to anhydrous ethanediol (12 mL), and the mixture was stirred at 60° C. for 3 hr. Then, 2-chloro-1-methyl-1H-benzimidazole (4.0 g) was added and the mixture was stirred with heating at 90° C. for 5 hr. The mixture was allowed to cool to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.0 g).

Workup

  1. stirringthe mixture was stirred
  2. temperaturewith heating at 90° C. for 5 hr
  3. temperatureto cool to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-00b06e84997c4c1aa7c0b98187431c8c
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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