Imidazole → 1-(2,4-dichlorophenyl)-2-(1H-imidazol-2-yl)ethanone

HRID 31809Notes

Reaction equation

HRID 31809 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:12])[CH2:10]Cl.[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>CC#N.ClCCl.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:12])[CH2:10][C:14]1[NH:13][CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 2

HCID 795ImidazoleHCID 202502,2',4'-Trichloroacetophenone

Product 1

HCID 221427181-(2,4-dichlorophenyl)-2-(1H-imidazol-2-yl)ethanoneYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 1-(2,4-dichlorophenyl)-2-chloroethan-1-one (0.95 M) and imidazole (2.68 M) in CH3CN (500 ml) were heated for 14-16 hours at 75° C. The product was stripped of solvent under reduced pressure. The residue was diluted with dichloromethane (1 L) and water (400 ml), and the mixture was stirred for 30 min. After filtering off a solid impurity, the aqueous layer was removed and discarded. The organic layer was washed sequentially with water (300 ml), sat. aq. NaHCO3 (300 ml), water (300 ml), brine (200 ml), dried with Na2SO4, filtered, and concentrated under reduced pressure. The reddish black oil was dried overnight in vacuo giving 1-(2,4-dichlorophenyl)-2-imidazolylethan-1-one in 90% yield.

Workup

  1. filtrationAfter filtering off a solid impurity
  2. customthe aqueous layer was removed
  3. washThe organic layer was washed sequentially with water (300 ml), sat. aq. NaHCO3 (300 ml), water (300 ml), brine (200 ml)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe reddish black oil was dried overnight in vacuo

Sources & evidence

ORD record
ord-19d31de134ae4192a4bfa98c276da4ac
Source dataset
uspto-grants-2008_09
Patent number
US07425557B2

Reaction notes

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