Sodium Iodide → 4-bromo-1-ethyl-5-(4-phthalimidobutyl)-1H-pyrazole-3-carbonitrile

HRID 1984358

Reaktionsgleichung

Reaktionsgleichung von HRID 1984358
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[I-].[Na+].[Br:15][C:16]1[C:17]([C:28]#[N:29])=[N:18][N:19]([CH2:26][CH3:27])[C:20]=1[CH2:21][CH2:22][CH2:23][CH2:24]Cl>C(Cl)(Cl)Cl.O.CN(C=O)C>[Br:15][C:16]1[C:17]([C:28]#[N:29])=[N:18][N:19]([CH2:26][CH3:27])[C:20]=1[CH2:21][CH2:22][CH2:23][CH2:24][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Komponenten

7

Edukt 3

HCID 5238Sodium Iodide2×HCID 24194345Phthalimide potassium salt2×HCID 669582654-bromo-5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile

Produkt 1

HCID 669584184-bromo-1-ethyl-5-(4-phthalimidobutyl)-1H-pyrazole-3-carbonitrileAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Potassium phthalimide (954 mg, 5.15 mmol), sodium iodide (130 mg, 0.86 mmol), and DMF (5 mL) were added to 4-bromo-5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile (1.0 g, 3.4 mmol, prepared as described in Parts A-E of Example 19), and the reaction was heated at 100° C. for 45 minutes under a nitrogen atmosphere and allowed to cool to ambient temperature. Water (50 mL) was added, and the resulting mixture was stirred at 0° C. A precipitate formed, was isolated by filtration, and was dissolved in chloroform. The resulting solution was dried over sodium sulfate, filtered, and concentrated under reduced pressure. An analysis by nuclear resonance spectroscopy (NMR) indicated that starting material was present. The solid was treated with potassium phthalimide (1.27 g, 6.88 mmol), sodium iodide (130 mg, 0.86 mmol), and DMF (5 mL) and heated at 90° C. for three hours. Water (50 mL) was added, and the resulting solid was isolated by filtration to provide 0.97 g of 4-bromo-1-ethyl-5-(4-phthalimidobutyl)-1H-pyrazole-3-carbonitrile as a gray, crystalline solid.

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. customA precipitate formed
  3. customwas isolated by filtration
  4. dry with materialThe resulting solution was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. temperatureheated at 90° C. for three hours
  8. customthe resulting solid was isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-cefe8cda0a8443deb6cdaf70932fc632
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544697B2

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