Sodium Methoxide → HCID 68663331, compound

HRID 452823Notes

Reaction equation

HRID 452823 reaction equation
CS([C:5]1[O:9][C:8]([C:10]2[CH:11]=[CH:12][C:13]3[N:17]=[CH:16][N:15]([C:18]4[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=4)[C:14]=3[CH:29]=2)=[N:7][N:6]=1)(=O)=O.[CH3:30][O-:31].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:30][O:31][C:5]1[O:9][C:8]([C:10]2[CH:11]=[CH:12][C:13]3[N:17]=[CH:16][N:15]([C:18]4[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=4)[C:14]=3[CH:29]=2)=[N:7][N:6]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 68662873HCID 68662873, compound

Product 1

HCID 68663331HCID 68663331, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-[5-(methylsulfonyl)-1,3,4-oxadiazol-2-yl]-1-[4-(trifluoromethoxy)phenyl]-1H-benzimidazole (150 mg, 0.35 mmol) in N,N-dimethylformamide (3 mL) was added sodium methoxide (23 mg, 0.42 mmol) at room temperature, and the resulting mixture was stirred for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=2/1-0/1) and recrystallized from hexane/ethyl acetate to give the title compound (35.4 mg, yield 27%) as colorless crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=2/1-0/1)
  5. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-1e2e0710e12c4e3dbdf456dd9cd244b0
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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