Pyridine → 3-Cyclooctyl-2,3,4,5,6,7-hexahydrocyclopenta[e]-1,3-oxazine-2,4-dione

HRID 1578925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1578925
[C:1](Cl)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[CH:11]1([N:19]=[C:20]=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.N1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[CH:11]1([N:19]2[C:1](=[O:9])[C:2]3[CH2:3][CH2:4][CH2:5][C:6]=3[O:7][C:20]2=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 61034Adipoyl chlorideHCID 12393370Cyclooctyl isocyanate

Produkt 1

HCID 123014413-Cyclooctyl-2,3,4,5,6,7-hexahydrocyclopenta[e]-1,3-oxazine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

With stirring and reflux cooling, 183 g (1 mole) of adipic acid chloride were added to a solution, kept at 120°C., of 168.6 g (1.1 moles) of cyclooctylisocyanate and 162 ml (2 moles) of pyridine in 500 ml of xylene. After 3 hours' reaction time, cooling was effected, followed by filtering off from the separated pyridine hydrochloride. The filtrate was first freed from solvent under reduced pressure and, finally, was distilled in a high vacuum. 158.2 g (60% of the theory) of 3-cyclooctyl-2,3,4,5,6,7-hexahydrocyclopenta[e]-1,3-oxazine-2,4-dione of the boiling point 172°-174°C/0.3 mm Hg were obtained when solidified to give a colorless crystal mass of the melting point 48°-51°C.

Aufarbeitung

  1. temperaturereflux
  2. temperaturecooling
  3. customAfter 3 hours' reaction time
  4. temperaturecooling
  5. filtrationby filtering off from the separated pyridine hydrochloride
  6. distillationfinally, was distilled in a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-68211dbf100b4c0fa9d39c7b702e4806
Quelldatensatz
uspto-grants-1976_02
Patentnummer
US03940390

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