1H-1,2,4-Triazole → alpha-((4-Chlorophenoxy)methyl)-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol

HRID 1087957

Reaktionsgleichung

Reaktionsgleichung von HRID 1087957
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]2([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:10][O:9]2)=[CH:4][CH:3]=1.[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1.[OH-].[K+]>C1(C)C=CC=CC=1.CS(C)=O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([OH:9])([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:10][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 92571H-1,2,4-TriazoleHCID 14797Potassium HydroxideHCID 127636212-tert-Butyl-2-[(4-chlorophenoxy)methyl]oxirane

Produkt 1

HCID 123676alpha-((4-Chlorophenoxy)methyl)-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanolAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 30 g of 2-(4-chlorophenoxymethyl)-2-tert.-butyloxirane, 9.8 g of 1,2,4-triazole and 1.2 g of solid potassium hydroxide in 70 ml of toluene and 7.5 ml of dimethyl sulphoxide was heated under reflux for 6 hours. After cooling to room temperature, 2 g of silica gel were added to the reaction mixture and it was then filtered. 75 ml of semi-concentrated hydrochloric acid were added to the filtrate, and the crystals which separated out thereby were filtered off with suction. Then 80 ml of water and aqueous sodium hydroxide solution were added to the crystalline solid so that the pH of the mixture was 13. It was stirred a further 2 hours at room temperature, then filtered off with suction and washed with water to neutrality. In this manner, 20 g (52% of theory) of 2-(4-chlorophenoxymethyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanol of melting point 84°-87° C. were obtained.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. addition2 g of silica gel were added to the reaction mixture and it
  4. filtrationwas then filtered
  5. addition75 ml of semi-concentrated hydrochloric acid were added to the filtrate
  6. customthe crystals which separated out
  7. filtrationthereby were filtered off with suction
  8. additionThen 80 ml of water and aqueous sodium hydroxide solution were added to the crystalline solid so that the pH of the mixture
  9. filtrationfiltered off with suction
  10. washwashed with water to neutrality

Quellen und Nachweise

ORD-Eintrag
ord-02ecf54870a2478091e2edb4090c6938
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04960911

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