Imidazole → 1-(2,4-Difluorophenyl)-2-(1H-imidazol-1-yl)ethan-1-one

HRID 1461406Notes

Reaction equation

HRID 1461406 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.ClC(Cl)Cl.Cl[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21])=[O:13]>O>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[C:12](=[O:13])[CH2:11][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6212Chloroform2×HCID 5880832-Chloro-1-(2,4-difluorophenyl)ethanone

Product 1

HCID 148725601-(2,4-Difluorophenyl)-2-(1H-imidazol-1-yl)ethan-1-oneYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a refluxing and stirred solution of 457.6 parts of 1H-imidazole in 2400 parts of trichloromethane was added dropwise a solution of 320 parts of 2-chloro-1-(2,4-difluorophenyl)ethanone in 1440 parts of trichloromethane. After stirring for 1/2 hour at reflux temperature, the reaction mixture was poured into water. The organic layer was washed with water (2x), dried, filtered and evaporated. The residue was crystallized from 2-propanol, yielding 244 parts (69%) of 1-(2,4-difluorophenyl)-2-(1H-imidazol-1-yl)ethanone; mp. 125° C. (interm. 1).

Workup

  1. temperatureat reflux temperature
  2. washThe organic layer was washed with water (2x)
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from 2-propanol

Sources & evidence

ORD record
ord-9133daeedc2c4e55aeaeb4fcc184920a
Source dataset
uspto-grants-1991_12
Patent number
US05075309

Reaction notes

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