Dimethylformamide → HCID 46942000, compound

HRID 735734Notes

Reaction equation

HRID 735734 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH3:12][C:13]1[N:14]=[CH:15][NH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:12][C:13]1[N:14]=[CH:15][N:16]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 67878Methyl 4-fluorobenzoateHCID 178418800HCID 178418800, compound

Product 1

HCID 46942000HCID 46942000, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of methyl 4-fluorobenzoate (1.00 g, 6.49 mmol), 4-methylimidazole (559 mg, 6.81 mmol), potassium carbonate (941 mg, 6.81 mmol) and DMF (30 ml) was stirred at 110° C. for 24 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was subjected to column chromatography using basic silica gel and eluted with ethyl acetate-methanol (1:0-1:1, v/v) to give the title compound (137 mg, 10%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous MgSO4
  3. concentrationconcentrated under reduced pressure
  4. washeluted with ethyl acetate-methanol (1:0-1:1

Sources & evidence

ORD record
ord-2d869d515a4048acbeab3aeba0bf1177
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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