Imidazole → HCID 43797885, compound

HRID 2228000Notes

Reaction equation

HRID 2228000 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:15])[CH2:11][N:12]([CH3:14])[CH3:13])=[CH:5][CH:4]=1.[NH:16]1C=CN=[CH:17]1>C(O)C.O>[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10](=[O:15])[CH2:11][N:12]2[CH:14]=[CH:17][N:16]=[CH:13]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 23179855HCID 23179855, compound

Product 1

HCID 43797885HCID 43797885, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of product from step B (7.80 g, 36.6 mmol) in ethanol (30 ml) and water (30 ml) containing imidazole (12.4 g, 183.0 mmol) was heated under reflux for 6 hrs. The mixture was allowed to cool and partitioned between dichloromethane (100 ml) and water (100 ml), the organic phase was washed with brine (5×100 ml) separated and dried (MgSO4). Evaporation of the residue left a yellow oil. This was purified by chromatography (Biotage flash 40, 90 g, SiO2 cartridge) eluting with a gradient of 0-5% methanol/dichloromethane to give 1-(4-fluorophenyl)-3-(imidazol-1-yl)propanone as a yellow oil 4.32 g (54%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hrs
  3. temperatureto cool
  4. custompartitioned between dichloromethane (100 ml) and water (100 ml)
  5. washthe organic phase was washed with brine (5×100 ml)
  6. customseparated
  7. dry with materialdried (MgSO4)
  8. customEvaporation of the residue
  9. waitleft a yellow oil
  10. customThis was purified by chromatography (Biotage flash 40, 90 g, SiO2 cartridge)
  11. washeluting with a gradient of 0-5% methanol/dichloromethane

Sources & evidence

ORD record
ord-613308c909364899aabcf12570e01686
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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