Cesium carbonate → 2-(2-Methyl-1H-benzimidazol-1-yl)ethan-1-ol

HRID 623998Notes

Reaction equation

HRID 623998 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:18][CH2:19][OH:20]>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[N:6]([CH2:18][CH2:19][OH:20])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 119842-Methylbenzimidazole

Product 1

HCID 7619262-(2-Methyl-1H-benzimidazol-1-yl)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-methyl-1H-benzimidazole (3.50 g, 25.95 mmol) in DMF (70.0 mL), Cs2CO3 (12.08 g, 36.33 mmol) and 2-bromoethanol (2.5 mL, 34.15 mmol) was added. After stirring at 150° C. for 1 h, the reaction mixture was allowed to reach rt and was diluted with EtOAc. The org. layer was separated and the aq. layer was extracted with EtOAc (5×). The combined org. layers were washed with brine, dried (MgSO4), filtered and the solvent was removed under reduced pressure to yield 2-(2-methyl-1H-benzoimidazol-1-yl)ethanol which was used in the next step without further purification. LC-MS conditions B: tR=0.25 min, [M+H]+=177.17.

Workup

  1. customto reach rt
  2. customlayer was separated
  3. extractionthe aq. layer was extracted with EtOAc (5×)
  4. washlayers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cb4474b38bf541eba65338aa05caf531
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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