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

HRID 1390415ノート

反応式

HRID 1390415 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6f5bd881cca44426ba100025021affea
出典データセット
uspto-grants-1979_02
特許番号
US04138569

反応ノート

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