Bromide ion → 1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-one

HRID 2166830Notes

Reaction equation

HRID 2166830 reaction equation
C(OCC)C.[CH3:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])=[O:8].[Br-].CO.[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1>>[Cl:16][C:10]1[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=1[C:7](=[O:8])[CH2:6][N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1

Participants

6

Reactant 5

HCID 259Bromide ionHCID 795ImidazoleHCID 887MethanolHCID 3283Diethyl EtherHCID 166932',4'-Dichloroacetophenone

Product 1

HCID 322321-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-oneYield 80%

Procedure

A 300 ml solution of diethyl ether containing 100 g (0.53 mole) of 2,4-dichloroacetophenone was cooled to 0°-5° C., and treated with 85.0 g (0.53 mole) of bromide and stirred one hour. The organic layer was washed with 3×500 ml portions of saturated sodium bicarbonate solution followed by 3×500 ml portions of water. The aqueous layer was removed and the organic layer treated with a 200 ml portion of methanol containing 108.0 g (1.6 mole) of imidazole and stirred in the cold overnight. The solution was concentrated, poured into 1600 ml of H2O with separation of an oil, the aqueous layer decanted, and the oil extracted 2×300 ml of methylene chloride. The combined organic phase was washed 2×300 ml of H2O, dried over magnesium sulfate and concentrated to give 108.8 g (80%) of a red oil. The nitrate salt was formed by treatment of the oil in acetone/ether solution with excess nitric acid, m.p. 161°-163° C. The free base obtained by neutralization was recrystallized from ethanol/water, m.p. 80°-82° C.

Workup

  1. washThe organic layer was washed with 3×500 ml portions of saturated sodium bicarbonate solution
  2. customThe aqueous layer was removed
  3. stirringstirred in the cold overnight
  4. concentrationThe solution was concentrated
  5. additionpoured into 1600 ml of H2O with separation of an oil
  6. customthe aqueous layer decanted
  7. extractionthe oil extracted 2×300 ml of methylene chloride
  8. washThe combined organic phase was washed 2×300 ml of H2O
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3dae7c5609f04b7bacf51a6054b169dd
Source dataset
uspto-grants-1983_06
Patent number
US04389409

Reaction notes

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