Triethylamine → 1-[2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-ethanone

HRID 1661932Notes

Reaction equation

HRID 1661932 reaction equation
C(Cl)(=O)C(Cl)=O.[CH:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]([CH2:21][CH2:22][O:23][CH3:24])[C:19]3[C:25]([O:32][CH3:33])=[CH:26][C:27]([CH:29]([OH:31])[CH3:30])=[CH:28][C:18]=3[N:17]=2)=[CH:12][CH:11]=1)([CH3:9])[CH3:8].C(N(CC)CC)C>ClCCl.CS(C)=O>[CH:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]([CH2:21][CH2:22][O:23][CH3:24])[C:19]3[C:25]([O:32][CH3:33])=[CH:26][C:27]([C:29](=[O:31])[CH3:30])=[CH:28][C:18]=3[N:17]=2)=[CH:12][CH:11]=1)([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 577720651-[2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-ethanol

Product 1

HCID 577720611-[2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-ethanoneYield 91.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-60 °C

Procedure

To a solution of 0.17 ml oxalylchloride in 4 ml dichloromethane, 0.285 ml DMSO (in 0.8 ml dichloromethane is slowly added at −60° C. This mixture is stirred under argon at −60° C. for 0.5 h. Then 180 mg (0.488 mmol) 1-[2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-ethanol (in 2 ml dichloromethane) are added and stirring is continued at −60° C. for 1 h. 1 ml triethylamine is added and the reaction mixture is allowed to warm to room temperature, poured on water and extracted (3×) with dichloromethane. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) to afford 163 mg of the title compound as a colorless oil.

Workup

  1. stirringstirring
  2. waitis continued at −60° C. for 1 h
  3. temperatureto warm to room temperature
  4. additionpoured on water
  5. extractionextracted (3×) with dichloromethane
  6. washThe combined organic layers are washed with water (2×) and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1)

Sources & evidence

ORD record
ord-e1335eb50554443bbd8c5c721d36f387
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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