Epichlorohydrin → HCID 20255175, compound

HRID 638054Notes

Reaction equation

HRID 638054 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[C:5]1[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26]([CH:28]1[O:30][CH2:29]1)Cl>>[O:30]1[CH2:29][CH:28]1[CH2:26][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:5]2[N:4]([CH2:3][CH2:2][OH:1])[CH:8]=[C:7]([C:9]([F:10])([F:12])[F:11])[N:6]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 136018549HCID 136018549, compound

Product 1

HCID 20255175HCID 20255175, compound

Procedure

A suspension of 3.26 g of 1-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-4-(trifluoromethyl)-1H-imidazole and 9.26 g of anhydrous potassium carbonate in 95 ml of epichlorohydrin is heated under reflux, while stirring, for 1 hour. The mixture is subsequently cooled in an ice bath, filtered and the filtrate freed of solvent in a rotary evaporator. The oil that remains behind is chromatographed on silica gel with ethyl acetate. The main fractions are combined and are caused to crystallise by the addition of hexane, yielding 2-[4-(2,3-epoxypropoxy)-phenyl]-1-(2-hydroxyethyl)-4-(trifluoromethyl)-1H-imidazole having a melting point of 110°-112°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperatureThe mixture is subsequently cooled in an ice bath
  4. filtrationfiltered
  5. customthe filtrate freed of solvent in a rotary evaporator
  6. customThe oil that remains behind is chromatographed on silica gel with ethyl acetate
  7. customto crystallise by the addition of hexane

Sources & evidence

ORD record
ord-d36852e8737343d5a37f0b931d6d2a87
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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