Epichlorohydrin → HCID 20255152, compound

HRID 638056Notes

Reaction equation

HRID 638056 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.C(=O)([O-])[O-].[K+].[K+].[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:23]=2)=[CH:15][CH:14]=1>>[O:5]1[CH2:4][CH:3]1[CH2:1][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:23]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 136136665HCID 136136665, compound

Product 1

HCID 20255152HCID 20255152, compound

Procedure

A mixture of 5 ml of epichlorohydrin and 0.5 g of potassium carbonate is heated under reflux. 0.5 g of 2-(4-hydroxyphenyl)-4-(trifluoromethyl)-thiazole is added in one portion and the reaction mixture is then heated under reflux for a further 15 minutes. After cooling, the mixture is filtered, the filtrate is concentrated by evaporation in a rotary evaporator and the residue is taken up in 6 ml of dichloromethane; 100 mg of tetrabutylammonium hydrogen sulphate and 6 ml of 2N sodium hydroxide solution are added to the solution and the whole is stirred for 3 hours at room temperature. The organic phase is separated off, washed and dried and finally the solvent is removed in a rotary evaporator. The residue is crystallised from ether/hexane yielding 2-[4-(2,3-epoxypropoxy)-phenyl]-4-(trifluoromethyl)-thiazole having a melting point of 97°-98°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperaturethe reaction mixture is then heated
  4. temperatureunder reflux for a further 15 minutes
  5. temperatureAfter cooling
  6. filtrationthe mixture is filtered
  7. concentrationthe filtrate is concentrated by evaporation in a rotary evaporator
  8. addition100 mg of tetrabutylammonium hydrogen sulphate and 6 ml of 2N sodium hydroxide solution are added to the solution
  9. customThe organic phase is separated off
  10. washwashed
  11. customdried
  12. customfinally the solvent is removed in a rotary evaporator
  13. customThe residue is crystallised from ether/hexane

Sources & evidence

ORD record
ord-b1adad90d6354855807efd2571c8d79a
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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