N-(2-Furoyl)Glycine → (4Z)-2-(2-furyl)-4-[(5-phenyl-2-furyl)methylene]-1,3-oxazol-5(4H)-one

HRID 1823954

Reaktionsgleichung

Reaktionsgleichung von HRID 1823954
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=O.C([O-])(=O)C.[Na+].[C:18]1([C:24]2[O:28][C:27]([CH:29]=O)=[CH:26][CH:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OC(=O)C)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:12][C:10](=[O:11])/[C:9](=[CH:29]/[C:27]2[O:28][C:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:25][CH:26]=2)/[N:8]=1

Komponenten

5

Edukt 3

HCID 21863N-(2-Furoyl)GlycineHCID 517045Sodium AcetateHCID 27694205-Phenyl-2-furaldehyde

Produkt 1

HCID 22148173(4Z)-2-(2-furyl)-4-[(5-phenyl-2-furyl)methylene]-1,3-oxazol-5(4H)-oneAusbeute 33,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

As illustrated in Scheme 2, N-2-furoylglycine (131 mg, 0.776 mmol) is suspended in acetic anhydride (1 mL) and sodium acetate (76 mg, 0.931 mmol) and 5-phenylfuraldehyde (170 mg, 1 mmol) are added. The reaction mixture is shaken at 60° C. for one hour, and cooled to 0° C. The resulting orange solid is filtered and washed with ice water (75 mL) and heptane (50 mL). The solid is then dried under vacuum at 40° C. to afford 79 mg of (4Z)-2-(2-furyl)-4-[(5-phenyl-2-furyl)methylene]-1,3-oxazol-5(4H)-one which was used without further purification.

Aufarbeitung

  1. temperaturecooled to 0° C
  2. filtrationThe resulting orange solid is filtered
  3. washwashed with ice water (75 mL) and heptane (50 mL)
  4. customThe solid is then dried under vacuum at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-c1baa3e6c33147469c37db0a4ec3b651
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07041690B2

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