Water → HCID 57656248, Verbindung

HRID 911578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911578
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:11]1[S:12][C:13]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:14]=2[N:15]=1)[CH:8]([CH3:10])[CH3:9].O.[OH-].[Na+]>C1COCC1>[NH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:13]2[S:12][C:11]([CH2:7][CH:8]([CH3:9])[CH3:10])=[N:15][C:14]=2[CH:16]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66707196HCID 66707196, Verbindung

Produkt 1

HCID 57656248HCID 57656248, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Add lithium aluminum hydride (0.78 mL, 0.78 mmol, 1M solution in THF) to 2-isobutyl-benzothiazole-5-carbonitrile (113 mg, 0.52 mmol) in THF (5 mL) and stir for 4 h at room temperature. Add water (0.27 mL), 2N sodium hydroxide (0.27 mL) and water (0.37 mL). Filter the precipitate and wash the filtrate with brine. Dry over Na2SO4 and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:1) and then 1M ammonia in methanol/dichloromethane (1:9). Purify the polar fraction by SCX chromatography to give the title compound (63 mg, 55%). MS (ES+) m/z: 221 (M+HE).

Aufarbeitung

  1. filtrationFilter the precipitate
  2. washwash the filtrate with brine
  3. dry with materialDry over Na2SO4
  4. concentrationconcentrate in vacuo
  5. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:1)
  6. customPurify the polar fraction by SCX chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c9370d32d73f4730a8dd8cf4d6d56fbc
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022062B2

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