4'-Fluoroacetophenone → Ethanone, 1-[4-(4-ethyl-1H-imidazol-1-yl)phenyl]-

HRID 505574Notes

Reaction equation

HRID 505574 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[N:6]=[CH:7][NH:8][CH:9]=1)[CH3:4].F[C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=1>CN(C=O)C.O>[CH2:3]([C:5]1[N:6]=[CH:7][N:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=2)[CH:9]=1)[CH3:4]

Participants

6

Reactant 3

HCID 98284'-FluoroacetophenoneHCID 24758Sodium hydrideHCID 178437183HCID 178437183, compound

Product 1

HCID 45095120Ethanone, 1-[4-(4-ethyl-1H-imidazol-1-yl)phenyl]-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

NaH (0.068 g in 60% oil dispersion, 1.7 mmol) was added to a solution of compound 16 (0.180 g, 1.8 mmol) in DMF (6 mL) with stirring at room temperature. The mixture was stirred for 15 min and a solution of 4′-fluoroacetophenone (0.215 g, 1.56 mmol) in DMF (2 mL) was added. The reaction mixture was heated at 80° C. for 1 h, and then cooled, diluted with water, and extracted with EtOAc. The organic layer was washed with brine, dried, and evaporated to a yellow solid. Compound 17 crystallized to form white color needles upon standing at room temperature. The yield was 0.270 g, 67%. The structure was confirmed by 1H NMR in CDCl3. LC-MS: [M+1]=215. Purity was >98%.

Workup

  1. stirringThe mixture was stirred for 15 min
  2. temperatureThe reaction mixture was heated at 80° C. for 1 h
  3. temperaturecooled
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. customdried
  7. customevaporated to a yellow solid
  8. customCompound 17 crystallized
  9. customto form white color needles
  10. customupon standing at room temperature

Sources & evidence

ORD record
ord-1ac89d2b9469471e84c1f554035ed69c
Source dataset
uspto-grants-2010_08
Patent number
US07781442B2

Reaction notes

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