Water → HCID 178518202, Verbindung

HRID 271396

Reaktionsgleichung

Reaktionsgleichung von HRID 271396
[Na].[C:2]1([CH:8]([C:12]([NH2:14])=[O:13])[C:9]([NH2:11])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15](OCC)=O.O>C(O)C>[C:2]1([C:8]2[C:12]([OH:13])=[N:14][CH:15]=[N:11][C:9]=2[OH:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8025Ethyl formateHCID 27475362-PhenylmalonamideHCID 5360545Sodium

Produkt 1

HCID 178518202HCID 178518202, VerbindungAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Sodium metal (0.92 g, 40 mmol) was dissolved by stirring in ethanol (30 mL) at room temperature under argon over 40 min. To the resulting solution at room temperature was added 2-phenylmalonamide (3.56 g, 20 mmol) and ethyl formate (1.9 mL, 24 mmol). The resulting suspension was heated at 50° C. under argon 16 h. After cooling the reaction mixture to room temperature, water (100 mL) was added and the mixture was stirred for 1 h. Solid was removed by filtration. The filtrate was acidified to pH˜4 with 1 M aqueous HCl. The resulting precipitate was collected by filtration and further washed with water (20 mL×2), then Et2O (10 mL×2). After drying under vacuum for 3 h, the title compound (2.6 g) was obtained as a light yellow solid. HPLC/MS: retention time=0.76 min, [M+H]+=189.

Aufarbeitung

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. customSolid was removed by filtration
  3. filtrationThe resulting precipitate was collected by filtration
  4. washfurther washed with water (20 mL×2)
  5. customAfter drying under vacuum for 3 h

Quellen und Nachweise

ORD-Eintrag
ord-688288197ef7443e83e0b009843faba2
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452892B2

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