Thionyl Chloride → HCID 178509686, Verbindung

HRID 846089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 846089
O[C:2]1([CH:7]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[C:8]2[N:9]=[N:10][NH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.S(Cl)(Cl)=O>ClCCl>[C:2]1(=[C:7]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[C:8]2[N:9]=[N:10][NH:11][CH:12]=2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 178509701HCID 178509701, Verbindung

Produkt 1

HCID 178509686HCID 178509686, VerbindungAusbeute 31,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

7.1 g of crude 4-[1-hydroxycyclopent-1-yl-1-(1,2,3-triazolyl)methyl]benzonitrile is dissolved at 0° in 50 ml of dichloromethane and stirred with 24 ml of thionyl chloride for 1 hour at 0°. Then the mixture is concentrated to dryness under vacuum, dissolved in 50 ml of dichloromethane, stirred with 32 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, yielding 2.1 g of 4-[1-cyclo-pentylidene-1-(1,2,3-triazolyl)methyl]benzonitrile as the free base, 108-109°.

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-20297bc8d0e14e34b494784e3c76532c
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05135937

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