Epichlorohydrin → 2-[4-(2,3-Epoxypropoxy)-phenyl]-thiazole

HRID 638059

反応式

HRID 638059 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[CH2:13]([CH:15]1[O:17][CH2:16]1)Cl.C(=O)([O-])[O-].[K+].[K+]>>[O:17]1[CH2:16][CH:15]1[CH2:13][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[CH:6][CH:7]=1

参加物

4

反応物 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 2238404-(1,3-Thiazol-2-yl)phenol

生成物 1

HCID 202551882-[4-(2,3-Epoxypropoxy)-phenyl]-thiazole

実験手順

0.5 g of 2-(4-hydroxyphenyl)-thiazole is added in one portion to a mixture, heated under reflux, of 5 ml of epichlorohydrin and 0.79 g of potassium carbonate and the reaction mixture is then heated under reflux for a further 20 minutes. After cooling, the mixture is filtered, the filtrate is concentrated by evaporation in a rotary evaporator and the residue is dissolved 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 with water and dried over sodium sulphate and the solvent is then removed in a rotary evaporator. The residue is recrystallised from a mixture of ether/hexane, yielding 2-[4-(2,3-epoxypropoxy)-phenyl]-thiazole having a melting point of 82°-93°.

後処理

  1. temperatureheated
  2. temperaturethe reaction mixture is then heated
  3. temperatureunder reflux for a further 20 minutes
  4. temperatureAfter cooling
  5. filtrationthe mixture is filtered
  6. concentrationthe filtrate is concentrated by evaporation in a rotary evaporator
  7. dissolutionthe residue is dissolved in 6 ml of dichloromethane
  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 with water
  11. dry with materialdried over sodium sulphate
  12. customthe solvent is then removed in a rotary evaporator
  13. customThe residue is recrystallised from a mixture of ether/hexane

出典と根拠

ORDレコード
ord-3ad6ddfd2762455b875c4f9449254a3f
出典データセット
uspto-grants-1985_12
特許番号
US04559354

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