Carbon Dioxide → HCID 21154053, Verbindung

HRID 2058533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2058533
[CH3:1][N:2]([CH3:22])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:13][C:12]([CH3:15])([CH3:14])[N:11]=[C:10]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:5][CH:4]=1.C(OC(=O)C)(=[O:25])C.OO.[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)=O>C(O)(=O)C>[CH3:22][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[O:13][C:12]([CH3:15])([CH3:14])[N+:11]([O-:25])=[C:10]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][CH:8]=1

Komponenten

8

Edukt 6

HCID 280Carbon DioxideHCID 784Hydrogen PeroxideHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 30614334-(2,2-Dimethyl-4-phenyl-2,5-dihydro-1,3-oxazol-5-yl)-N,N-dimethylaniline

Produkt 1

HCID 21154053HCID 21154053, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 70.2 g of 5-[p-(dimethylamino)-phenyl]-2,2-dimethyl-4-phenyl-3-oxazoline in 300 ml of glacial acetic acid was added while stirring to a mixture, cooled to 0° C., of 30 ml of acetic anhydride and 90 m. of 30% hydrogen peroxide. The mixture was then stirred at room temperature for an additional 2.5 hours, treated while cooling with sodium hydroxide (342 g of sodium hydroxide in 2 liters of water) and sufficient sodium carbonate was added until carbon dioxide no longer evolved. Then, the mixture was evaporated almost to dryness on a rotary evaporator in a water-jet vacuum at 60° C., and the residue was extracted with 2.5 liters of dichloromethane. The dichloromethane solution was dried over sodium sulfate, filtered and evaporated in a water-jet vacuum. The residue was chromatographed on silica gel, the elution being carried out firstly with acetone and subsequently with methanol. The fractions containing the product were combined and largely freed from solvent in a water-jet vacuum. There were thus obtained 52 g of a hygroscopic oil from which a part of the water was removed at room temperature and 0.1 Torr (4 hours). Crystallization was then carried out twice from acetone, the solution being decolorized with active carbon. The crystalline product was dried for 16 hours at 70° C. and 0.1 Torr, and there were obtained 40.8 g of 5-[p-(dimethylamino)phenyl]-2,2-dimethyl-4-phenyl-3-oxazoline N-oxide in the form of hygroscopic white crystals which decomposed during the melting from 130° C.

Aufarbeitung

  1. stirringThe mixture was then stirred at room temperature for an additional 2.5 hours
  2. additiontreated
  3. customThen, the mixture was evaporated almost to dryness on a rotary evaporator in a water-jet vacuum at 60° C.
  4. extractionthe residue was extracted with 2.5 liters of dichloromethane
  5. dry with materialThe dichloromethane solution was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in a water-jet vacuum
  8. customThe residue was chromatographed on silica gel
  9. washthe elution
  10. additionThe fractions containing the product
  11. customwas removed at room temperature
  12. custom0.1 Torr (4 hours)
  13. customCrystallization
  14. customThe crystalline product was dried for 16 hours at 70° C.

Quellen und Nachweise

ORD-Eintrag
ord-e22c23edd1bf48a7955003c283eaf8e5
Quelldatensatz
uspto-grants-1982_03
Patentnummer
US04317914

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