Imidazole → HCID 13232348, compound

HRID 358076Notes

Reaction equation

HRID 358076 reaction equation
Br[CH2:2][C:3]1([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:5]([C:6]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=2[Cl:13])[O:4]1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.C[O-].[Na+]>CN(C)C=O>[N:21]1([CH2:2][C:3]2([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:5]([C:6]3[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=3[Cl:13])[O:4]2)[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 10942334Sodium MethoxideHCID 13232347HCID 13232347, compound

Product 1

HCID 13232348HCID 13232348, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 10 g of 2-bromomethyl-2-(4-chlorophenyl)-3-(2,4-dichlorophenyl)-oxirane (isomer A) in 50 mL of N,N-dimethylformamide was added dropwise, at 100° C., to a melt which comprised 15.6 g of imidazole with 1.37 g of sodium methylate and from which the liberated methanol had been distilled off beforehand. 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, dried over sodium sulfate and evaporated down under reduced pressure, and the residue was chromatographed over a silica gel column using methylene chloride/methanol (100:2). The purified fractions were evaporated down, and the residue was crystallized from diisopropyl ether. 4.6 g (47.5%) of 2-(1H-imidazol-1-yl-methyl)-2-(4-chlorophenyl)-3-(2,4-dichlorophenyl)-oxirane (isomer A) of melting point 102°-103° C. were obtained (compound 1).

Workup

  1. distillationfrom which the liberated methanol had been distilled off beforehand
  2. additionthe reaction solution was poured onto water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated down under reduced pressure
  7. customthe residue was chromatographed over a silica gel column
  8. customThe purified fractions were evaporated down
  9. customthe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-a7b41322a2e64a2c9f0fc6eedbc5f823
Source dataset
uspto-grants-1984_08
Patent number
US04464381

Reaction notes

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