Thionyl Chloride → HCID 178509688, Verbindung

HRID 846087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 846087
O[C:2]1([CH:8]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[C:9]2[N:10]=[N:11][NH:12][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.S(Cl)(Cl)=O>ClCCl>[C:2]1(=[C:8]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[C:9]2[N:10]=[N:11][NH:12][CH:13]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 178509702HCID 178509702, Verbindung

Produkt 1

HCID 178509688HCID 178509688, VerbindungAusbeute 36,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

7.6 g of crude 4-[1-hydroxycyclohex-1-yl-1-(1,2,3-triazolyl)methyl]benzonitrile is dissolved at 0° in 50 ml of dichloromethane and stirred at 0° for 1 hour with 22.7 ml of thionyl chloride. Then the mixture is concentrated to dryness under vacuum, dissolved in 50 ml of dichloromethane, stirred with 30 ml of triethylamine for 2 hours, diluted with water, extracted three times with ethyl acetate, washed with water, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with hexane/ethyl acetate, thus obtaining 2.6 g of 4-[1-cyclohexylidene-1-(1,2,3-triazolyl)methyl]benzonitrile as the free base. 132-133° C.

Aufarbeitung

  1. concentrationThen the mixture is concentrated to dryness under vacuum
  2. dissolutiondissolved in 50 ml of dichloromethane
  3. additiondiluted with water
  4. extractionextracted three times with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness under vacuum
  8. customchromatographed on silica gel with hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-511b6afe65df4f54bc617d8761805b41
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05135937

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