Aluminium lithium hydride → HCID 59828852, Verbindung

HRID 1191077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191077
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:25])([F:24])[CH2:9][NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[N:15]=1>C1COCC1>[F:25][C:8]([F:7])([F:24])[CH2:9][NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:17]=[CH:18][C:19]([CH2:20][NH2:21])=[CH:22][CH:23]=2)[N:15]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 59828836HCID 59828836, Verbindung

Produkt 1

HCID 59828852HCID 59828852, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Add lithium aluminum hydride (402 mg, 10.6 mmol) portionwise over 3 min to a solution of 4-[2-(2,2,2-trifluoroethylamino)-thiazol-4-yl]-benzonitrile (1.0 g, 3.5 mmol) in THF (40 mL) at room temperature under a nitrogen atmosphere. Stir the mixture for 1 h at 55° C. Cool the mixture to room temperature, quench slowly with water (0.4 mL) and 1N NaOH (0.4 mL). Add sodium sulfate to absorb residual water, filter through Celite®, wash with DCM (50 mL) and concentrate in vacuo. Purify the residue by SCX chromatography to obtain the desired intermediate (902 mg, 90%). MS (ES+) m/z: 288 (M+H)+.

Aufarbeitung

  1. temperatureCool the mixture to room temperature
  2. customquench slowly with water (0.4 mL) and 1N NaOH (0.4 mL)
  3. customAdd sodium sulfate to absorb residual water
  4. filtrationfilter through Celite®
  5. washwash with DCM (50 mL)
  6. concentrationconcentrate in vacuo
  7. customPurify the residue by SCX chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cc909f33cb8f4b15bd885f8f74ef401b
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680091B2

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