Water → 2-[4-(2,3-Epoxypropoxy)-phenyl]-1-methyl-4-(trifluoromethyl)-imidazole

HRID 638024Notes

Reaction equation

HRID 638024 reaction equation
[H-].[Na+].[O:3]1[CH2:22][CH:4]1[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:17]=2)=[CH:9][CH:8]=1.[CH3:23]I.O>CN(C)C=O>[O:3]1[CH2:22][CH:4]1[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]([CH3:23])[CH:15]=[C:16]([C:18]([F:20])([F:19])[F:21])[N:17]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178506251HCID 178506251, compound

Product 1

HCID 202550772-[4-(2,3-Epoxypropoxy)-phenyl]-1-methyl-4-(trifluoromethyl)-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g of sodium hydride dispersion (55% in oil) are added, while cooling in an ice bath, to a solution of 12 g of 2-[4-(2,3-epoxypropoxy)-phenyl]-4-(trifluoromethyl)-imidazole (J. med. Chem. 20, 1024 (1977)) in 90 ml of dimethylformamide and the yellow suspension is stirred for 11/2 hours at room temperature. After the addition of 8 ml of methyl iodide, stirring is continued for a further 12 hours at room temperature, the reaction mixture is subsequently poured into water and extracted several times with ethyl acetate. After separating off the organic phase and removing the solvent, the residue is dissolved in chloroform and filtered over silica gel. The filtrate is again concentrated by evaporation and the residue is recrystallized from ether/hexane, yielding 2-[4-(2,3-epoxypropoxy)-phenyl]-1-methyl-4-(trifluoromethyl)-imidazole having a melting point of 65°-68°.

Workup

  1. stirringstirring
  2. waitis continued for a further 12 hours at room temperature
  3. extractionextracted several times with ethyl acetate
  4. customAfter separating off the organic phase
  5. customremoving the solvent
  6. dissolutionthe residue is dissolved in chloroform
  7. filtrationfiltered over silica gel
  8. concentrationThe filtrate is again concentrated by evaporation
  9. customthe residue is recrystallized from ether/hexane

Sources & evidence

ORD record
ord-22a45c56a7aa49c594fe9a5b026b8fe6
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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