Water → 4-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

HRID 234904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 234904
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]2[NH:9][C:10](=[O:13])[CH2:11][O:12][C:7]=2[CH:6]=1)=[O:4].[H-].[Na+].[CH2:18](I)[CH3:19].O>CN(C)C=O.C(OCC)(=O)C>[CH2:18]([N:9]1[C:8]2[CH:14]=[CH:15][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][C:7]=2[O:12][CH2:11][C:10]1=[O:13])[CH3:19]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 10845978Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate

Produkt 1

HCID 107761024-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazineAusbeute 26,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine [prepared in Preparation 4(1)] (1.0 g) in dimethylformamide (80 ml) were added 60% sodium hydride (in oil) (0.25 g) and ethyl iodide (1.0 g) and the mixture was stirred at room temperature for a day. Water was added to the reaction solution and extraction with ethyl acetate was conducted. The solvent was distilled off under reduced pressure and the resulting residue was recrystallized from ethyl acetate/hexane to give 4-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (0.3 g).

Aufarbeitung

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe resulting residue was recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-b0c323f87f274e5c912556c8f1bc1267
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597820

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