Water → 5-[3-(Bicyclo[2.2.1]hept-2-yloxy]-4-Methoxyphenyl]2,4-Imidazolidinedione
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-:19]#[N:20].[Na+].[C:22](=[O:25])([O-])[O-].[NH4+:26].[NH4+].[OH2:28]>C(O)C>[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:26][C:19](=[O:28])[NH:20][C:22]2=[O:25])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]Participants
6
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 NCl 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
- temperatureThe reaction is cooled
- extractionthe product extracted 2× ethyl acetate
- washThe collected organics are washed with water, brine
- concentrationconcentrated in vacuo
- dissolutionThe solid is redissolved in ethyl acetate
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customthe resulting crude oil triturated from ether
Sources & evidence
- ORD record
- ord-4a1cd2abf7f6403b93779d277d18f3d1
- Source dataset
- uspto-grants-1995_10
- Patent number
- US05459145
Reaction notes
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