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

HRID 614668Notes

Reaction equation

HRID 614668 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8e16bb95d1104134bbb08ed69ef20280
Source dataset
uspto-grants-1979_03
Patent number
US04145510

Reaction notes

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