Methanol → 2-Butyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

HRID 416591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 416591
[CH2:1]([N:5]1[C:14](=O)[C:13]([C:16]#[N:17])=[C:12]2[C:7]([CH:8](O)[CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1.CO>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:14](=[S:28])[C:13]([C:16]#[N:17])=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 87949Lawesson's reagentHCID 222665102-Butyl-8-hydroxy-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

Produkt 1

HCID 222665172-Butyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrileAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

2-Butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-013) (80 mg, 0.35 mmol) was dissolved in toluene (8 mL), and to the reaction mixture was added Lawesson's reagent (169 mg, 0.42 mmol), the reaction mixture was heated under reflux for 12 h. The reaction mixture was cooled to room temperature, and methanol was added to the reaction mixture, and the reaction mixture was stirred at room temperature for 1 h, and evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 2-butyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-014) (63 mg, 73%) as a pale brown powder.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 12 h
  3. customevaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-96af06376f93472ebc0ba07f408fa3c7
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088924B2

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