Imidazole → HCID 13232348, compound

HRID 358077Notes

Reaction equation

HRID 358077 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[CH2:9][C:10]1([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[O:11]1.[I-].[K+]>CN(C)C=O>[N:1]1([CH2:9][C:10]2([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[O:11]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 13232347HCID 13232347, compound

Product 1

HCID 13232348HCID 13232348, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6.2 g of imidazole and 1.3 g of sodium hydride (50% strength dispersion in mineral oil) were dispersed in 50 ml of N,N-dimethylformamide, and a solution of 12 g of 2-bromomethyl-2-(4-chlorophenyl)-3-(2,4-dichlorophenyl)-oxirane (isomer B) and 5 g of potassium iodide in 50 ml of N,N-dimethylformamide was added at room temperature (20° C.). After 8 hours, the reaction solution was poured onto water and the mixture was extracted with ethyl acetate. The organic phase was washed with water and dried over sodium sulfate, the solvent was evaporated off under reduced pressure and the residue was recrystallized from diisopropyl ether. 9.4 g (82.5%) of 2-(1H-imidazol-1-yl-methyl)-2-(4-chlorophenyl)-3-(2,4-dichlorophenyl)-oxirane (isomer B) of melting point 109° C. were obtained (compound 2).

Workup

  1. additionthe reaction solution was poured onto water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated off under reduced pressure
  6. customthe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-5c00229d9ada4f7f978248b74411cc68
Source dataset
uspto-grants-1984_08
Patent number
US04464381

Reaction notes

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