Potassium Cyanide → 5-(2-Diethylphosphonoethyl)-5-methylhydantoin

HRID 614667Notes

Reaction equation

HRID 614667 reaction equation
O=[C:2]([CH3:13])[CH2:3][CH2:4][P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].[C-]#N.[K+].[C:17](=[O:20])([O-])[O-].[NH4+:21].[NH4+:22].[CH2:23]([OH:25])C.O>>[CH2:7]([O:6][P:5]([CH2:4][CH2:3][C:2]1([CH3:13])[NH:22][C:23](=[O:25])[NH:21][C:17]1=[O:20])([O:9][CH2:10][CH3:11])=[O:12])[CH3:8]

Participants

5

Reactant 4

HCID 9032Potassium CyanideHCID 14033Diethyl (3-oxobutyl)phosphonateHCID 517111Ammonium CarbonateHCID 19096565Water ethanol

Product 1

HCID 539367345-(2-Diethylphosphonoethyl)-5-methylhydantoin

Procedure

A mixture of 208 grams (1 mole) of diethyl 3-oxobutylphosphonate, 130 grams (2 moles) of potassium cyanide, and 456 grams (4.75 moles) of ammonium carbonate dissolved in 2200 ml of 50:50 ethanol-water was heated and stirred under nitrogen at reflux for five hours. After the heating period, the reaction mixture was stripped in vacuo at 70° C./16 mm and the residue dried at 75° C./0.1 mm. Anhydrous ethanol, 1100 ml, was added to the residue and the mixture boiled until only inorganic salts remained undissolved. The suspension was cooled and then filtered. The clear filtrate was cooled to 5°-10° C. and anhydrous hydrogen chloride was bubbled in until the mixture had a pH of about 2. The resulting turbid solution was warmed at 40°-50° C. with 25 grams of charcoal and refiltered. The ethanol solution was then heated in vacuo to give a viscous syrup, 246 grams. The crude syrup was recrystallized from ethyl acetate to give a white crystalline product in a yield of 145 grams (52% of theory), m.p. 100°-103° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for five hours
  3. customwas stripped in vacuo at 70° C.
  4. customthe residue dried at 75° C./0.1 mm
  5. additionAnhydrous ethanol, 1100 ml, was added to the residue
  6. temperatureThe suspension was cooled
  7. filtrationfiltered
  8. temperatureThe clear filtrate was cooled to 5°-10° C.
  9. customanhydrous hydrogen chloride was bubbled in until the mixture
  10. temperatureThe resulting turbid solution was warmed at 40°-50° C. with 25 grams of charcoal
  11. temperatureThe ethanol solution was then heated in vacuo
  12. customto give a viscous syrup, 246 grams
  13. customThe crude syrup was recrystallized from ethyl acetate
  14. customto give a white crystalline product in a yield of 145 grams (52% of theory), m.p. 100°-103° C.

Sources & evidence

ORD record
ord-63d29d13d44d47e1a2aac16984f8c5a7
Source dataset
uspto-grants-1979_03
Patent number
US04145510

Reaction notes

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