Acetamide → 7-methyl-4-(2-methyl-1,3-oxazol-4-yl)-2H-chromen-2-one

HRID 2422516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422516
Br[CH2:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([CH3:15])=[CH:12][CH:13]=2)[O:8][C:7](=[O:16])[CH:6]=1)=O.[C:17]([NH2:20])(=[O:19])[CH3:18].C(OCC)(=O)C>CN(C)C=O>[CH3:15][C:11]1[CH:10]=[C:9]2[C:14]([C:5]([C:3]3[N:20]=[C:17]([CH3:18])[O:19][CH:2]=3)=[CH:6][C:7](=[O:16])[O:8]2)=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 178AcetamideHCID 8857Ethyl AcetateHCID 866219744-(bromoacetyl)-7-methyl-2H-chromen-2-one

Produkt 1

HCID 866219757-methyl-4-(2-methyl-1,3-oxazol-4-yl)-2H-chromen-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 4-(bromoacetyl)-7-methyl-2H-chromen-2-one (750 mg, 2.67 mmol) in N,N-dimethylformamide (2.5 mL), acetamide (158 mg, 2.67 mmol) was added. The reaction was then stirred overnight at 100° C. After cooling, the reaction mixture was dissolved with ethyl acetate and washed with water and brine, dried over MgSO4, filtered and concentrated. The crude residue obtained was pre-adsorbed on silica gel and purified by column chromatography (EtOAc/hexanes, 30:70 to 80:20) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 8.52 (s, 1H), 8.21 (d, 1H), 7.23 (s, 1H), 7.21 (d, 1H), 6.52 (s, 1H), 2.57 (s, 3H), 2.49 (s, 3H).

Aufarbeitung

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue obtained
  7. custompurified by column chromatography (EtOAc/hexanes, 30:70 to 80:20)

Quellen und Nachweise

ORD-Eintrag
ord-bde0578f06204f3ea4e1fc509bb4d86f
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960409B2

Notizen zur Reaktion

Wird geladen…