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

HRID 839178노트

반응식

HRID 839178 반응식
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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-e1039c04b81542ae882efbbdab9fcfd5
출처 데이터셋
uspto-grants-1978_06
특허 번호
US04093809

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