Ethanol → Diethyl (1,1-dimethyl-2-(4-methyl-2,5-dioxoimidazolidin-4-yl)ethyl)phosphonate

HRID 839179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 839179
[CH3:1][C:2]([P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])([CH3:7])[CH2:3][C:4](=O)[CH3:5].[CH2:16]([OH:18])C.[C-]#N.[K+].[C:22](=[O:25])([O-])[O-].[NH4+:26].[NH4+:27]>O>[CH3:5][C:4]1([CH2:3][C:2]([P:8]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])=[O:15])([CH3:7])[CH3:1])[NH:27][C:22](=[O:25])[NH:26][C:16]1=[O:18]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 153111314-Methyl-4-diethylphosphonopentan-2-one

Produkt 1

HCID 6455210Diethyl (1,1-dimethyl-2-(4-methyl-2,5-dioxoimidazolidin-4-yl)ethyl)phosphonateAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A suspension of 23.6 grams (0.1 mole) of diethyl 1,1-dimethyl-3-oxobutylphosphonate [A. N. Pudovick, Zh. Obshch. Khim., 22, 1371 (1952)], 40 ml of ethanol, 30 ml of water, 9.8 grams (0.15 mole) of potassium cyanide and 28.8 grams (0.3 mole) of powdered ammonium carbonate was heated at 60° C for six hours. The reaction mixture was cooled and filtered to remove suspended salts. The filtrate was neutralized with hydrochloric acid, and evaporated to dryness. Residual inorganic salts were removed by dissolving the residue in methylene chloride and followed by filtration. The product was then isolated by evaporation of the solvent and drying to yield 19.5 grams (64%) of 5-methyl-5-(2-diethylphosphono-2-methylpropyl)hydantoin, m.p. 142°-146° C. Recrystallization from ethyl acetate raised the m.p. to 146°-148.5° C.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customto remove
  4. customevaporated to dryness
  5. customResidual inorganic salts were removed
  6. dissolutionby dissolving the residue in methylene chloride
  7. filtrationfollowed by filtration
  8. customThe product was then isolated by evaporation of the solvent
  9. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-983cb354c94247d09f8154c01a60a236
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093809

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