Formaldehyde → 1-(4-Chlorophenylthio)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pentan-3-one

HRID 255812

Reaktionsgleichung

Reaktionsgleichung von HRID 255812
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[CH3:9][C:10]([C:13]([CH2:15][N:16]1[N:20]=[CH:19][N:18]=[CH:17]1)=[O:14])([CH3:12])[CH3:11].C=O.N1CCCC[CH2:24]1>C1(C)C=CC=CC=1.O.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:24][CH:15]([N:16]2[CH:17]=[N:18][CH:19]=[N:20]2)[C:13](=[O:14])[C:10]([CH3:9])([CH3:11])[CH3:12])=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 712FormaldehydeHCID 7815p-ChlorothiophenolHCID 8082PiperidineHCID 1008773,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone

Produkt 1

HCID 131913651-(4-Chlorophenylthio)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pentan-3-oneAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 72.5 g (0.5 mol) of 4-chlorothiophenol, 100.2 g (0.6 mol) of 1,2,4-triazol-1-yl-pinacolin, 18 g (0.6 mol) of paraformaldehyde, 15 g of acetic acid and 5 ml of piperidine in 600 ml of toluene was heated under reflux in a water separator. After the water has been separated off, the reaction solution was washed with water, dried over sodium sulphate, filtered, and concentrated in vacuo. The oily residue was chromatographed over a silica gel column (mobile phase: chloroform). 45 g (28% of theory) of 1-(4-chlorophenylthio)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan -3-one of melting point 67° C. were obtained.

Aufarbeitung

  1. temperaturewas heated
  2. customAfter the water has been separated off
  3. washthe reaction solution was washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe oily residue was chromatographed over a silica gel column (mobile phase: chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-928c673c32af4ee084ea5f08ee68500e
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04699645

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