Hydrochloric Acid → 5-[3-(Bicyclo[2.2.1]hept-2-yloxy]-4-Methoxyphenyl]2,4-Imidazolidinedione

HRID 653650Notes

Reaction equation

HRID 653650 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=O.[C-]#N.[Na+].[C:22](=[O:25])([O-])[O-].[NH4+:26].[NH4+:27].Cl.[CH2:29]([OH:31])C>O>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[O:8][C:9]1[CH:10]=[C:11]([CH:12]2[NH:27][C:29](=[O:31])[NH:26][C:22]2=[O:25])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8929Sodium CyanideHCID 517111Ammonium CarbonateHCID 140101523-(Bicyclo[2.2.1]hept-2-yloxy)-4-methoxybenzaldehyde

Product 1

HCID 140101735-[3-(Bicyclo[2.2.1]hept-2-yloxy]-4-Methoxyphenyl]2,4-ImidazolidinedioneYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(Bicyclo[2.2.1]hept-2-yloxy)-4-Methoxybenzaldehyde (20.0 g, 81.3 mmol), sodium cyanide (8.0 g, 162.6 mmol) and ammonium carbonate (32.0 g, 333.3 mmol) are dissolved in 100 ml ethanol and 100 ml water and refluxed for 4 hours. The reaction is cooled, neutralized with 1N HCl solution and the product extracted 2× ethyl acetate. The collected organics are washed with water, brine and concentrated in vacuo. The solid is redissolved in ethyl acetate, dried over Na2SO4, concentrated in vacuo and the resulting crude oil triturated from ether to produce 18.3 g (71%) of the hydantoin as a crystalline material. This material is a 7:3 endo/exo mixture of bicycloalkyl isomers.

Workup

  1. temperatureThe reaction is cooled
  2. extractionthe product extracted 2× ethyl acetate
  3. washThe collected organics are washed with water, brine
  4. concentrationconcentrated in vacuo
  5. dissolutionThe solid is redissolved in ethyl acetate
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customthe resulting crude oil triturated from ether

Sources & evidence

ORD record
ord-dc7b15cc632646eea1715a2762df2872
Source dataset
uspto-grants-1992_07
Patent number
US05128358

Reaction notes

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