Hydantoin → 3-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxybenzylidene-2,4-imidazolidinedione

HRID 1884502Notes

Reaction equation

HRID 1884502 reaction equation
[NH:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].N1CCCC1.[CH3:13][C:14]1[C:15]([C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=2[O:36][CH3:37])[CH:31]=O)=[CH:16][C:17]2[C:18]([CH3:27])([CH3:26])[CH2:19][CH2:20][C:21]([CH3:25])([CH3:24])[C:22]=2[CH:23]=1>C(O)C>[CH3:13][C:14]1[C:15]([C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=2[O:36][CH3:37])[CH:31]=[C:5]2[NH:1][C:2](=[O:7])[NH:3][C:4]2=[O:6])=[CH:16][C:17]2[C:18]([CH3:27])([CH3:26])[CH2:19][CH2:20][C:21]([CH3:24])([CH3:25])[C:22]=2[CH:23]=1

Participants

5

Reactant 3

HCID 10006HydantoinHCID 31268PyrrolidineHCID 112791263-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4-methoxy-benzaldehyde

Product 1

HCID 694623563-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxybenzylidene-2,4-imidazolidinedione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,4-imidazolidinedione (101 mg, 1.0 mmol), pyrrolidine (0.04 mL, 0.5 mmol) and 3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4-methoxy-benzaldehyde (336 mg, 1.0 mmol) in ethanol (15 mL) was heated under reflux for 24 hours, allowed to cool to room temperature and extracted with ethyl acetate (2×100 mL). The organic extracts were washed with saturated aqueous NH4Cl (60 mL), saturated NH4Cl (70 mL), saturated aqueous NaCl (60 mL), dried over MgSO4 and filtered. Removal of the solvent under reduced pressure gave a yellow solid that was purified by column chromatography, using a Biotage 40S cartridge, eluting with ethyl acetate/hexane (3:7). The title compound was isolated as a yellow solid (270 mg, 65%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. washThe organic extracts were washed with saturated aqueous NH4Cl (60 mL), saturated NH4Cl (70 mL), saturated aqueous NaCl (60 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customRemoval of the solvent under reduced pressure
  8. customgave a yellow solid
  9. customthat was purified by column chromatography
  10. washeluting with ethyl acetate/hexane (3:7)

Sources & evidence

ORD record
ord-1f34f05479134da9b175076a33ba2d64
Source dataset
uspto-grants-2004_07
Patent number
US06765013B2

Reaction notes

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