Triphenylphosphine → (2-Methyl-5-nitro-phenyl)-(5-pyridin-3-yloxazol-2-yl)-amine

HRID 2237638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2237638
[N:1]([CH2:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:6])=[N+]=[N-].[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[N:23]=[C:24]=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[NH:23][C:24]1[O:6][C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][N:1]=1

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 2926092-Methyl-5-nitrophenyl isocyanateHCID 593028753-Azidoacetylpyridine

Produkt 1

HCID 59302880(2-Methyl-5-nitro-phenyl)-(5-pyridin-3-yloxazol-2-yl)-amineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 3-azidoacetylpyridine (800 mg, 4.94 mmol) in dioxane 10 mL was added 2-methyl-5-nitrophenyl isocyanate (880 mg, 4.94 mmol) (commercially available), and triphenylphosphine (1.29 g, 4.94 mmol). The reaction mixture was placed in an oil bath preheated to 100° C. and stirred for 30 min. After evaporation of the solvent under reduced pressure the residue was partitioned between 4N HCl (20 mL) and dichloromethane (20 mL). The aqueous layer was neutralized with 15% NaOH and extracted with dichloromethane (3×20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous MgSO4, concentrated. The residue was silica gel column chromatographed (dichloromethane/ethanol:97/3) to give the title compound as yellow micro crystals (1.14 g, 78%).

Aufarbeitung

  1. customThe reaction mixture was placed in an oil bath
  2. custompreheated to 100° C.
  3. customAfter evaporation of the solvent under reduced pressure the residue
  4. customwas partitioned between 4N HCl (20 mL) and dichloromethane (20 mL)
  5. extractionextracted with dichloromethane (3×20 mL)
  6. washThe combined organic layers were washed with brine (20 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated
  9. customchromatographed (dichloromethane/ethanol:97/3)

Quellen und Nachweise

ORD-Eintrag
ord-16bfb3d726b34845b0fe20538d53142d
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718676B2

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