Water → HCID 178418322, Verbindung

HRID 1449571

Reaktionsgleichung

[Na].O=[C:3]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:15][C:16]1[C:25]2[NH:24]C(=O)[O:22][C:21](=O)[C:20]=2[CH:19]=[CH:18][CH:17]=1.O>CN(C)C=O>[Cl:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:21]2[OH:22]

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

To a stirred mixture of diethyl oxosuccinate sodium salt (2.31 g, 11.0 mM) in dimethylformamide (20 mL) under a nitrogen atmosphere was added 8-chloro-2H-3,1-benzoxazine-2,4(1H)-dione (2.17 g, 11.0 mM). The resulting mixture was heated slowly to 130° C. and maintained at this temperature for 2.5 hr. After cooling, the reaction mixture was poured into water and the resulting mixture was then extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried (MgSO4), filtered and concentrated to obtain an oily solid (1.55 g). This material was chromatographed (eluant: CH2C12 /CH3OH; 98/2) over silica gel to provide the title compound as an oil which slowly crystallized to a tan solid (0.700 g, 19.7%). A 0.150 g portion of this material was recrystallized from toluene/hexane to provide an analytical sample (0.050 g) of the title compound as a tan solid, mp 98°-99° C.; MS(CI): 324 (M+H).

Aufarbeitung

temperaturemaintained at this temperature for 2.5 hr
temperatureAfter cooling
extractionthe resulting mixture was then extracted with ethyl acetate
washThe combined organic extracts were washed with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-928a9dc9f80d4312b080180228a5bc9d
Quelldatensatz: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05599814

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