Allyl chloride → 1,3-Diallyl-5,5-dimethylhydantoin

HRID 1862952

Reaktionsgleichung

Reaktionsgleichung von HRID 1862952
[H-].[Na+].[CH2:3]([N:6]1[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[NH:8][C:7]1=[O:14])[CH:4]=[CH2:5].[H][H].[CH2:17](Cl)[CH:18]=[CH2:19]>O.CN(C=O)C>[CH2:19]([N:8]1[C:9]([CH3:13])([CH3:12])[C:10](=[O:11])[N:6]([CH2:3][CH:4]=[CH2:5])[C:7]1=[O:14])[CH:18]=[CH2:17]

Komponenten

7

Edukt 4

HCID 7850Allyl chlorideHCID 24758Sodium hydrideHCID 5976963-Allyl-5,5-dimethylhydantoinHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 9200291,3-Diallyl-5,5-dimethylhydantoin

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a slurry of 4.8 grams (0.1 mole) of a 50% sodium hydride mineral oil dispersion in 35 ml. of DMF was added portionwise with stirring 17.6 grams (0.105 mole) of 3-allyl-5,5-dimethylhydantoin. Hydrogen was evolved in this exothermic reaction. The reaction mixture was heated and stirred at 55°-60° C. for 1 hour till the gas evolution ceased and a clear solution resulted. To the solution was added dropwise with stirring over a 10-minute period keeping the temperature below 80° C. 9.3 grams (0.12 mole) of allyl chloride. The reaction mixture was then heated at 55°-60° C. for 1.5 hours. Following cooling to room temperature, the reaction mixture was poured into 100 ml of water. An oily product was formed which was extracted using benzene and purified by vacuum distillation. The above named product was obtained in a yield of 14.15 grams (68%) boiling at 89°-92° C./0.1 mm. (Compound 3)

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. customa clear solution resulted
  3. additionTo the solution was added dropwise
  4. stirringwith stirring over a 10-minute period
  5. customthe temperature below 80° C
  6. temperatureThe reaction mixture was then heated at 55°-60° C. for 1.5 hours
  7. customAn oily product was formed which
  8. extractionwas extracted
  9. distillationpurified by vacuum distillation
  10. customwas obtained in a yield of 14.15 grams (68%) boiling at 89°-92° C./0.1 mm

Quellen und Nachweise

ORD-Eintrag
ord-4bf0f6d9855a4f14a9d4d0f5c390f321
Quelldatensatz
uspto-grants-1979_09
Patentnummer
US04167465

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