Epichlorohydrin → 2-[4-(2,3-epoxypropoxy)-phenyl]-1-methyl-5-(trifluoromethyl)-1H-imidazole

HRID 638049Notes

Reaction equation

HRID 638049 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:17])[C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:24]([CH:26]1[O:28][CH2:27]1)Cl>>[O:28]1[CH2:27][CH:26]1[CH2:24][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:17])[C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 1360029642-(4-hydroxyphenyl)-1-methyl-5-(trifluoromethyl)-1H-imidazole

Product 1

HCID 202551182-[4-(2,3-epoxypropoxy)-phenyl]-1-methyl-5-(trifluoromethyl)-1H-imidazole

Procedure

25 g of the 2-(4-hydroxyphenyl)-1-methyl-5-(trifluoromethyl)-1H-imidazole obtained according to Example (20c) and 25 g of anhydrous potassium carbonate are suspended in 250 ml of epichlorohydrin and the mixture is heated under reflux for 10 minutes. The mixture is subsequently filtered and excess epichlorohydrin is removed in a rotary evaporator. The residue is dissolved in ether, the solution is stirred with silica gel and active carbon, the solution is filtered and hexane is added until crystallisation begins. After filtration, 2-[4-(2,3-epoxypropoxy)-phenyl]-1-methyl-5-(trifluoromethyl)-1H-imidazole is obtained in the form of a colourless crystallisate having a melting point of 99°-101°.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 10 minutes
  3. filtrationThe mixture is subsequently filtered
  4. customexcess epichlorohydrin is removed in a rotary evaporator
  5. dissolutionThe residue is dissolved in ether
  6. filtrationthe solution is filtered
  7. additionhexane is added until crystallisation
  8. filtrationAfter filtration

Sources & evidence

ORD record
ord-98547ad911fd49588c5d549fbdbe7183
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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