Ethyl Acetate → HCID 21834409, Verbindung

HRID 1740966

Reaktionsgleichung

Reaktionsgleichung von HRID 1740966
Cl[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:13])([CH3:12])[N:3]=1.[CH2:14]([C:16]1[CH:17]=[N+:18]([O-])[CH:19]=[CH:20][CH:21]=1)[CH3:15].C(OCC)(=[O:25])C>C(Cl)Cl>[CH2:14]([C:16]1[CH:21]=[CH:20][C:19]([N:3]2[C:2](=[O:25])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[O:5][C:4]2([CH3:13])[CH3:12])=[N:18][CH:17]=1)[CH3:15]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 84685Pyridine, 3-ethyl-, 1-oxideHCID 6020844-chloro-2,2-dimethyl-2H-1,3-benzoxazine

Produkt 1

HCID 21834409HCID 21834409, VerbindungAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 172 mg (0.87 mmol) of 4-chloro-2,2-dimethyl-(2H)-1,3-benzoxazine (K. Wachi and A. Terada, Chem. Pharm. Bull, 1980, 28, 465-472) and 215 mg (1.75 mmol) of 3-ethylpyridine N-oxide (S. Hibino and E. Sugino, J. Heterocycl Chem., 1990, 27, 175) in 1.6 mL of methylene chloride was heated to reflux for 9 h with stirring. After cooling the reaction, 30 mL ethyl acetate was added and the mixture was washed in succession with 10 mL saturated sodium bicarbonate and 10 mL of saturated aqueous sodium chloride. The organic solution was dried (sodium sulfate), decanted, and evaporated to give a yellow liquid. Flash column chromatography on 17 g of silica gel, eluting with 100 mL of 5% ethyl acetate/hexane and 500 mL of 7% ethyl acetate/hexane furnished 84 mg (33% yield) of 3-(5-ethyl-2-pyridinyl)-2,2-dimethyl-2,3-dihydro-(4H)-1,3-benzoxazin-4-one as a colorless syrup.

Aufarbeitung

  1. temperatureto reflux for 9 h
  2. temperatureAfter cooling
  3. additionwas added
  4. washthe mixture was washed in succession with 10 mL saturated sodium bicarbonate and 10 mL of saturated aqueous sodium chloride
  5. dry with materialThe organic solution was dried (sodium sulfate)
  6. customdecanted
  7. customevaporated
  8. customto give a yellow liquid
  9. washFlash column chromatography on 17 g of silica gel, eluting with 100 mL of 5% ethyl acetate/hexane and 500 mL of 7% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-371d704204f246d19d9a55bfd8ea0d24
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05972975

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