Lawesson's reagent → Ethyl 3-(3,4-difluorophenyl)-2-thioxopiperidine-3-carboxylate

HRID 1398140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398140
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[F:23][C:24]1[CH:25]=[C:26]([C:31]2([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:36][CH2:35][CH2:34][NH:33][C:32]2=O)[CH:27]=[CH:28][C:29]=1[F:30]>C1(C)C=CC=CC=1>[F:23][C:24]1[CH:25]=[C:26]([C:31]2([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:36][CH2:35][CH2:34][NH:33][C:32]2=[S:10])[CH:27]=[CH:28][C:29]=1[F:30]

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 66607999Ethyl 3-(3,4-difluorophenyl)-2-oxopiperidine-3-carboxylate

Produkt 1

HCID 86662973Ethyl 3-(3,4-difluorophenyl)-2-thioxopiperidine-3-carboxylateAusbeute 116,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Under an argon atmosphere, Lawesson's reagent (1.00 g) was added to a suspension of ethyl 3-(3,4-difluorophenyl)-2-oxopiperidine-3-carboxylate (1.00 g) in toluene (20 ml) at room temperature. The reaction mixture was stirred at 110° C. for 4 hr, and allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (859 mg).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-634c1c9ada60448d8eab2c696764435e
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901309B2

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