4-[1-Hydroxycyclopent-1-yl-1-(imidazolyl)methyl]benzonitrile → 4-[1-Cyclopentylidene-1(imidazolyl)methyl]benzonitrile

HRID 1198165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1198165
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[NH:9][CH:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1>S(Cl)(Cl)=O>[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[NH:9][CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

3

Edukt 1

HCID 544681894-[1-Hydroxycyclopent-1-yl-1-(imidazolyl)methyl]benzonitrile

Produkt 1

HCID 542154114-[1-Cyclopentylidene-1(imidazolyl)methyl]benzonitrileAusbeute 48,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

6.9 g of crude 4-[1-hydroxycyclopent-1-yl-1-(imidazolyl)methyl]benzonitrile is refluxed in 82 ml of thionyl chloride to 0.5 hour. Then the mixture is concentrated to dryness under vacuum, combined with 2 N sodium hydroxide solution, extracted with dichloromethane, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with hexane/ethyl acetate, thus producing 3.1 g of 4-[1-cyclopentylidene-1-(imidazolyl)methyl]benzonitrile as the free base, mp 108°-110°.

Aufarbeitung

  1. concentrationThen the mixture is concentrated to dryness under vacuum
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customchromatographed on silica gel with hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b2bb78e4ff31481c81b8e95ff26f7821
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05280035

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