Ethanol → HCID 21328251, compound

HRID 839181Notes

Reaction equation

HRID 839181 reaction equation
O=[C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4]([P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])([CH3:10])[CH2:3]1.[C-]#N.[K+].[C:22](=[O:25])([O-])[O-].[NH4+:26].[NH4+:27].[CH2:28]([OH:30])C>O>[CH3:10][C:4]1([P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])[CH2:5][C:6]([CH3:9])([CH3:8])[CH2:7][C:2]2([NH:27][C:28](=[O:30])[NH:26][C:22]2=[O:25])[CH2:3]1

Participants

6

Reactant 4

HCID 702EthanolHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 23462695HCID 23462695, compound

Product 1

HCID 21328251HCID 21328251, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A suspension of 829 grams (3 moles) of diethyl 3-oxo-1,5,5-trimethylcyclohexylphosphonate (A. N. Pudovik and I. V. Konovalova, Zh. Obshch. Khim., 27, 1617 (1957), 293 grams (4.5 moles) of potassium cyanide, and 864 grams (9 moles) of powdered ammonium carbonate in 1200 ml of ethanol and 900 ml of water, was heated to 55° C with stirring over a period of 30 minutes. The mixture was heated at 55° C for an additional 5.5 hours, cooled to room temperature and filtered through a Buchner funnel. The resulting two diastereomeric hydantoin derivatives (isomers A and B) which differ in solubilities and melting points were then isolated, respectively, from the filter cake and filtrate.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a Buchner funnel
  3. customwere then isolated

Sources & evidence

ORD record
ord-65da3d4ec45a49eaad4d2881183be157
Source dataset
uspto-grants-1978_06
Patent number
US04093809

Reaction notes

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