2-Phenylcyclohexanone → 4a-phenyl-4a,5,6,7-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione

HRID 451124Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451124
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](Cl)([N:16]=[C:17]=[O:18])=[O:15]>C(OCC)(=O)C>[C:1]1([CH:7]2[C:8]3[O:13][C:17](=[O:18])[NH:16][C:14](=[O:15])[C:9]=3[CH2:10][CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([C:7]23[CH2:12][CH2:11][CH2:10][CH:9]=[C:8]2[O:13][C:17](=[O:18])[NH:16][C:14]3=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 955922-PhenylcyclohexanoneHCID 119708Isocyanatocarbonyl chloride

Produkt 2

HCID 105143688-phenyl-5,6,7,8-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dioneAusbeute 19,62 %HCID 105381824a-phenyl-4a,5,6,7-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dioneAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A solution of 2-phenylcyclohexanone (1.500 g, 8.61 mmol) and carbonisocyanatidic chloride (0.966 mL, 12 mmol) was stirred at 58° C. in a high-pressure vessel (75 mL) for 1 h. The temperature was raised to 130° C. and the reaction mixture was stirred for 2 h. After cooling to room temperature, the reaction mixture solidified. The solid residue was dissolved in ethyl acetate and washed with saturated aqueous solution of sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuum and the oily residue was purified by column chromatography on silica gel to provide 8-phenyl-5,6,7,8-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione (415.0 mg, 1.689 mmol, 19.62% yield) as white solid and 4a-phenyl-4a,5,6,7-tetrahydro-2H-benzo[e][1,3]oxazine-2,4(3H)-dione (746.4 mg, 3.04 mmol, 35.3% yield) as white solid.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washwashed with saturated aqueous solution of sodium bicarbonate
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed in vacuum
  8. customthe oily residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ece7c552872f43cb8632bcaa31b47b50
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486952B2

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