Potassium Cyanide → 4-Benzyloxycyclohexanone hydantoin

HRID 2393937Notes

Reaction equation

HRID 2393937 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](=[O:19])([O-])[O-].[NH4+:20].[NH4+:21].[C-]#N.[K+]>C(O)C>[NH:20]1[CH2:13][C:12](=[O:15])[NH:21][C:16]1=[O:19].[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 109873694-(Benzyloxy)cyclohexanone

Product 1

HCID 702323244-Benzyloxycyclohexanone hydantoin

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

4-Benzyloxycyclohexanone 41 is dissolved in 30 mL of 50% ethanol containing ammonium carbonate and potassium cyanide is added (Step 38). The mixture will be warmed to 60° C. for 2 h and evaporated to dryness in vacuo. The residue is extracted with 40 mL of hot methanol, filtered, and the filter cake washed with 20 mL of hot methanol. The methanol solutions are combined, solvent evaporated, and the residue chromatographed on silica gel using CH2Cl2 /methanol 90:10 to yield 42.

Workup

  1. additionis added (Step 38)
  2. customevaporated to dryness in vacuo
  3. extractionThe residue is extracted with 40 mL of hot methanol
  4. filtrationfiltered
  5. washthe filter cake washed with 20 mL of hot methanol
  6. customsolvent evaporated
  7. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-23e582c50aa0497d81bc657785601a97
Source dataset
uspto-grants-1998_09
Patent number
US05808146

Reaction notes

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