Epichlorohydrin → HCID 20255178, compound

HRID 638029Notes

Reaction equation

HRID 638029 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[N:7]([CH3:10])[C:8]=1[CH3:9])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:24]([CH:26]1[O:28][CH2:27]1)Cl>CN(C)C=O>[C:1]([C:4]1[N:5]=[C:6]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:24][CH:26]3[O:28][CH2:27]3)=[CH:15][CH:16]=2)[N:7]([CH3:10])[C:8]=1[CH3:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 136139251HCID 136139251, compound

Product 1

HCID 20255178HCID 20255178, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 11.5 g of 4-acetyl-1,5-dimethyl-2-(4-hydroxyphenyl)-1H-imidazole, 13.8 g of potassium carbonate, 7.0 g of epichlorohydrin and 120 ml of dimethylformamide is stirred for 20 hours in a bath at 60°-70°. The insoluble material is filtered off, the filtrate is concentrated by evaporation and the residue is divided between ethyl acetate and water. From the organic phase there is obtained, by concentration by evaporation, an oil which is chromatographed on silica gel with ethyl acetate. 4-acetyl-1,5-dimethyl-2-[4-(2,3-epoxypropoxy)-phenyl]-1H-imidazole is obtained from the first six fractions eluted in the form of a yellow oil.

Workup

  1. filtrationThe insoluble material is filtered off
  2. concentrationthe filtrate is concentrated by evaporation
  3. customFrom the organic phase there is obtained, by concentration by evaporation
  4. customan oil which is chromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-e041db18f85440719744b57d65133dd0
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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