Sodium Chloride → 1H,4H,5H,6H-cyclopenta[c]pyrazole-3-carbonitrile

HRID 475500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475500
[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[C:3]([C:9]([NH2:11])=O)=[N:2]1.[Cl-].[Na+].P(Cl)(Cl)(Cl)=O>C(#N)C>[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[C:3]([C:9]#[N:11])=[N:2]1

Komponenten

5

Edukt 3

HCID 5234Sodium ChlorideHCID 24813Phosphorus oxychlorideHCID 451212581H,4H,5H,6H-cyclopenta[c]pyrazole-3-carboxamide

Produkt 1

HCID 231351391H,4H,5H,6H-cyclopenta[c]pyrazole-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1,4,5,6-Tetrahydro-cyclopentapyrazole-3-carboxylic acid amide (0.210 g, 1.39 mmol) was added to anhydrous acetonitrile (12 cm3), heated to 80° C. and sodium chloride (2.0 g, 34-mmol) added. After 15 minutes phosphorus oxychloride (0.128 g, 0.83 mmol) was added and the solution heated to 80° C. overnight, cooled, filtered, and the collected solid washed with acetonitrile. Solvent was removed from the combined solutions under reduced pressure and the resulting solid purified by preparative HPLC to give 1,4,5,6-tetrahydro-cyclopentapyrazole-3-carbonitrile as a deep purple coloured solid (0.031 g, 0.23 mmol, 17%). δH (CD3OD): 2.79 (t like, 2H, J=7.3), 2.73 (t like, 2H, J=7.1), 2.65-2.55 (m, 2H); m/z (ES+): 134 [M+H]+.

Aufarbeitung

  1. temperaturethe solution heated to 80° C. overnight
  2. temperaturecooled
  3. filtrationfiltered
  4. washthe collected solid washed with acetonitrile
  5. customSolvent was removed from the combined solutions under reduced pressure
  6. customthe resulting solid purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b715a3541ca34ee298e9497ac23a7e2f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637555B2

Notizen zur Reaktion

Wird geladen…