Benzamide → Ethyl (2-phenyl-1,3-oxazol-4-yl)acetate

HRID 4399

Reaktionsgleichung

Reaktionsgleichung von HRID 4399
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:11][C:12](=O)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)(O)[O-].[Na+]>>[C:2]1([C:1]2[O:8][CH:11]=[C:12]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 2331BenzamideHCID 69484Ethyl 4-chloroacetoacetateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 15567335Ethyl (2-phenyl-1,3-oxazol-4-yl)acetateAusbeute 38 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of benzamide (60.0 g) and ethyl 4-chloroacetoacetate (49.4 g) was heated at 120° C. for 2 hours. After cooling, aqueous sodium bicarbonate solution was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated. The residue was purified by chromatography on silica gel with ethyl ether-hexane (1:9) to yield ethyl 2-phenyl-4-oxazoleacetate as an oil (26.4 g, 28.0%). NMR (CDCl3)δ: 1.27 (3H, t, J=7 Hz), 3.68 (3H, s), 4.15 (2H, q, J=7 Hz), 7.4 (3H, m), 7.67 (1H, s), 8.0 (2H, m).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel with ethyl ether-hexane (1:9)

Quellen und Nachweise

ORD-Eintrag
ord-e63f4e4c221e4ca7857dee83451d2403
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725610

Verknüpfte Notizen

Wird geladen…