Sodium hydride → HCID 21462570, Verbindung

HRID 375524

Reaktionsgleichung

Reaktionsgleichung von HRID 375524
[H-].[Na+].[CH2:3]([C:5]1([C:18]([F:21])([F:20])[F:19])[CH2:10][NH:9][C:8]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:7]=2[O:6]1)[CH3:4].Cl.Cl[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N+:25]=1[O-:30]>CS(C)=O>[CH2:3]([C:5]1([C:18]([F:21])([F:20])[F:19])[CH2:10][N:9]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N+:25]=2[O-:30])[C:8]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:7]=2[O:6]1)[CH3:4]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 88478Chloride 2-chloropyridinium 1-oxideHCID 21462569HCID 21462569, Verbindung

Produkt 1

HCID 21462570HCID 21462570, VerbindungAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Sodium hydride (0.68 g, 60% in mineral oil) was added to a solution of 2-ethyl-2-trifluoromethyl-6-nitro-3,4-dihydro-2H-1,4-benzoxazine (0.235 g), 2-chloropyridine-N-oxide hydrochloride (0.142 g), and dimethylsulfoxide (10 mL) and stirred at room temperature overnight. The mixture was quenched with saturated ammonium chloride/water and extracted into ethyl acetate. The organic extract was washed (water, brine) dried, decolorized (charcoal), filtered (celite) and evaporated. Chromatography, eluting successively with dichloromethane, ethyl acetate, and then methanol, gave the title compound as a yellow solid (0.11 g); mp 59°-62° C.; NMR: 0.95 (t,3), 2.04 (q), 4.05 (d,d), 7.01 (s,1), 7.25 (d) 7.45 (m,2), 7.63 (d), 7.76 (d), 8.41 (d,1); MS: m/z=370(M+1). Analysis for C16H14F3N3O4 : Calculated: C, 52.04; H, 3.82; N, 11.38; Found: C, 51.95; 3.98; N, 11.10.

Aufarbeitung

  1. customThe mixture was quenched with saturated ammonium chloride/water
  2. extractionextracted into ethyl acetate
  3. extractionThe organic extract
  4. washwas washed (water, brine)
  5. customdried
  6. filtrationfiltered (celite)
  7. customevaporated
  8. washChromatography, eluting successively with dichloromethane, ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4bf7d2431d7f45b4a7e2a2eeab8a5352
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05486515

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