Phosphorus sulfide (P2S5) → Methyl 4-amino-4-thioxobutanoate

HRID 1397300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397300
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][CH2:3][C:4]([NH2:6])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:11]>C1COCC1>[NH2:6][C:4](=[S:11])[CH2:3][CH2:2][C:1]([O:8][CH3:9])=[O:7]

Komponenten

4

Edukt 2

HCID 14817Phosphorus sulfide (P2S5)HCID 12550576Methyl 3-carbamoylpropanoate

Produkt 1

HCID 18333020Methyl 4-amino-4-thioxobutanoateAusbeute 55,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl succinamate (2 g, 15.2 mmol) was dissolved in dry THF (50 mL) and P2S5 (3.4 g, 15.2 mmol) was added and the reaction mixture was stirred at room temperature for 6 h. The reaction mixture was filtered through a sintered funnel and the clear filtrate was concentrated under reduced pressure to get the crude product, which was further purified by column chromatography (silica gel 60-120 mesh, eluent 50% EtOAc in petroleum ether) to afford methyl 4-amino-4-thioxobutanoate (1.25 g, yield 53%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.27 (br s, 2H), 3.72 (s, 3H), 2.96-2.85 (m, 4H). MS (ESI) m/z: Calculated for C5H9NO2S: 147.04. found: 148.2 (M+H)+.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a sintered funnel
  2. concentrationthe clear filtrate was concentrated under reduced pressure
  3. customto get the crude product, which
  4. customwas further purified by column chromatography (silica gel 60-120 mesh, eluent 50% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-69f6d4b76c954659a7591d6102157aad
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901156B2

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