Sodium hydride → 2-(2-Ethyl-2-trifluoromethyl-6-nitro-3,4-dihydro-2H-1,4-benzoxazine-4-yl)pyridine-N-oxide

HRID 1940510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1940510
[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 214625692-ethyl-2-trifluoromethyl-6-nitro-3,4-dihydro-2H-1,4-benzoxazine

Produkt 1

HCID 214625702-(2-Ethyl-2-trifluoromethyl-6-nitro-3,4-dihydro-2H-1,4-benzoxazine-4-yl)pyridine-N-oxideAusbeute 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-b0b2a7d262af40ba8406bab79d8e80db
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05700798

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