Water → 2-Amino-4,5-bis(furan-2-yl)oxazole

HRID 421032

Reaktionsgleichung

Reaktionsgleichung von HRID 421032
[CH:1]1[CH:5]=[C:4]([CH:6]([OH:14])[C:7]([C:9]2[O:13][CH:12]=[CH:11][CH:10]=2)=O)[O:3][CH:2]=1.[N:15]#[C:16][NH2:17].[O-]CC.[Na+].O>C(O)C>[NH2:17][C:16]1[O:14][C:6]([C:4]2[O:3][CH:2]=[CH:1][CH:5]=2)=[C:7]([C:9]2[O:13][CH:12]=[CH:11][CH:10]=2)[N:15]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 9864CyanamideHCID 11100FuroinHCID 2723922Sodium ethoxide

Produkt 1

HCID 126152352-Amino-4,5-bis(furan-2-yl)oxazoleAusbeute 31,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Furoin (0.50 g, 2.60 mmol) was dissolved in ethanol (15 mL). Cyanamide (218.8 mg, 5.20 mmol) and sodium ethoxide (530.8 mg, 7.80 mmol) were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (hexane:ethyl acetate=1:1→1:2) to give the title compound (175.0 mg, 31.1%) as a dark brown crystal.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe residue obtained by evaporation under reduced pressure
  5. customwas purified by chromatography on silica gel (hexane:ethyl acetate=1:1→1:2)

Quellen und Nachweise

ORD-Eintrag
ord-ab0765434ba74cbdb554c4afadea7153
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097759B2

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