2-Methylimidazole → HCID 18324431, compound

HRID 1251900Notes

Reaction equation

HRID 1251900 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[F:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](=[O:15])[CH2:13]Br)=[CH:10][CH:9]=1>C(OCC)(=O)C.O>[F:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](=[O:15])[CH2:13][N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 127492-MethylimidazoleHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one

Product 1

HCID 18324431HCID 18324431, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 2-methylimidazole (8.0 g, 97.5 mmol) and 4-fluorophenacyl bromide (21.16 g, 97.5 mmol) dissolved in ethyl acetate (40 ml) at ambient temperature was treated with tiethylamine (16.4 ml, 117 mmol) and the cloudy mixture heated at reflux for 16 hours. The mixture was cooled to ambient temperature and diluted with ethyl acetate and water, washed with water and brine, dried and evaporated to dryness. The residue was recrystallised (3×) from dichloromethane/methanol/isohexane to give 1-(4-fluorophenyl)-2-(2-methylimidazol-1-yl)ethanone (1, 9.0 g, 42%).

Workup

  1. additionwas treated with tiethylamine (16.4 ml, 117 mmol)
  2. temperaturethe cloudy mixture heated
  3. temperatureat reflux for 16 hours
  4. washwashed with water and brine
  5. customdried
  6. customevaporated to dryness
  7. customThe residue was recrystallised (3×) from dichloromethane/methanol/isohexane

Sources & evidence

ORD record
ord-8de14b1767ef49a38a8f9e5d8407d3ce
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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