Imidazole → HCID 13232348, compound

HRID 1906486Notes

Reaction equation

HRID 1906486 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; cf. Example b) in 50 ml of N,N-dimethylformamide was added dropwise, at 100° C., to a melt consisting of 15.6 g of imidazole and 1.37 g of sodium methylate, the methanol liberated having been distilled off from the melt beforehand. After 8 hours, the reaction solution was poured onto water and 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 a 100:2 methylene chloride/methanol mixture. The purified fractions were evaporated down, and the residue was crystallized from diisopropyl ether. 4.6 g (47.5%) of 2-(1H-imidazol-1-ylmethyl)-2-(4-chlorophenyl)-3-(2,4-dichlorophenyl)-oxirane (isomer A) of melting point 102°-103° C. were obtained.

Workup

  1. distillationthe methanol liberated having been distilled off from the melt beforehand
  2. additionthe reaction solution was poured onto water
  3. extractionextracted 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-8bd94ce79cb748699cf41e9811ab5e0b
Source dataset
uspto-grants-1987_03
Patent number
US04652580

Reaction notes

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