2-Bromoacetamidopyridine → 2-(3-Chlorophenyl)-4-(pyridin-2-yl)-1,3-oxazole

HRID 431898

Reaktionsgleichung

Reaktionsgleichung von HRID 431898
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)=O.[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([NH2:17])=[O:16]>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:13]=[C:14]([C:15]2[O:16][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=3)[N:17]=2)[CH:18]=[CH:19][CH:20]=1

Komponenten

4

Edukt 2

HCID 383842-BromoacetamidopyridineHCID 692543-Chlorobenzamide

Produkt 1

HCID 102207452-(3-Chlorophenyl)-4-(pyridin-2-yl)-1,3-oxazoleAusbeute 24,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Using the procedures of Kelly et al., J. Org. Chem., (1996) 61:4623-4633, a solution of 2-bromoacetylpyridine (120 mg, 0.6 mmol) in toluene (5 mL) was treated with 3-chlorobenzamide (300 mg, 1.9 mmol) and the mixture heated in a sealed vial at reflux for 60 hours. The mixture was then cooled and the solvent was removed in vacuo. Silica gel chromatography using a gradient of hexane to ethyl acetate afforded 38 mg (9%) of 2-[3-chlorophenyl]-4-[pyridin-2-yl]-1,3-oxazole as a pale yellow solid. 1H-NMR (CDCl3), δ (ppm): 8.62 (d, 1H), 8.35 (s, 1H), 8.15 (m, 1H), 8.00 (m, 2H), 7.80 (td, 1H), 7.42 (m, 2H), 7.23 (m, 1H).

Aufarbeitung

  1. temperaturethe mixture heated in a sealed vial
  2. temperatureat reflux for 60 hours
  3. temperatureThe mixture was then cooled
  4. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5a4391cd3386466e96efcf6ba2193b0c
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660753B2

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