Water → 4,5-Dihydro-4-oxo-N-phenyl-2-(phenylamino)-3-furancarboxamide

HRID 231127

Reaktionsgleichung

Reaktionsgleichung von HRID 231127
[H-].[Na+].[C:3]1([N:9]=[C:10]=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O.Br[CH2:14][C:15](=[O:26])[CH2:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18]>O1CCOCC1>[O:26]=[C:15]1[CH2:14][O:11][C:10]([NH:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[C:16]1[C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7672Phenyl isocyanateHCID 24758Sodium hydrideHCID 2682684-Bromo-3-oxo-n-phenylbutanamide

Produkt 1

HCID 141985354,5-Dihydro-4-oxo-N-phenyl-2-(phenylamino)-3-furancarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

Under a nitrogen atmosphere, sodium hydride (97%; 0.633 g, 25.61 mmol) was weighed into a dry reaction vessel and covered with 55 ml of anhydrous dioxane. A solution of phenyl isocyanate (1.39 ml, 12.81 mmol) in 5 ml of anhydrous dioxane was then added over a 5-10 minute period at room temperature (cooling with cold water). Next, the 4-bromoacetoacetanilide (3.28 g, 12.8 mmol) was added portionwise over a 20-minute period. The reaction mixture was stirred at 20°-25° C. for 5 hours, filtered under nitrogen atmosphere, and poured into 300 ml of ice-cold water. After acidifying (pH 5-6) with several drops of concentrated hydrochloric acid, the crude product was filtered off and crystallized from ethanol to provide 2.8 g. of amide product, m.p. 182°-184° C.

Aufarbeitung

  1. filtrationfiltered under nitrogen atmosphere
  2. additionpoured into 300 ml of ice-cold water
  3. filtrationthe crude product was filtered off
  4. customcrystallized from ethanol
  5. customto provide 2.8 g

Quellen und Nachweise

ORD-Eintrag
ord-727b3696ee3c4956a2b6d68519769f7d
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845122

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