Ethanol → HCID 22117520, compound

HRID 1275788Notes

Reaction equation

HRID 1275788 reaction equation
[C:1]1([C:7]2([CH2:20][CH2:21]C=O)[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:24]#[N:25].[K+].[C:27](=[O:30])([O-])[O-].[NH4+:31].[NH4+].[CH2:33]([OH:35])C>>[C:8]1([C:7]2([CH2:20][CH2:21][CH:24]3[NH:25][C:33](=[O:35])[NH:31][C:27]3=[O:30])[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:2]3[C:1]2=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 22117471HCID 22117471, compound

Product 1

HCID 22117520HCID 22117520, compoundYield 30%

Conditions

Temperature
60 °C

Procedure

A mixture of 0.3 g (1 mmol) of 3-(9-phenyl-9H-fluoren-9-yl)propanal (from Step 2), 0.07 g (1.1 mmol) potassium cyanide and 0.23 g (2.4 mmol) ammonium carbonate in 50% aqueous ethanol (5 mL) was placed in a pressure tube and heated at 60° C. for 16 h with stirring. The reaction was then cooled to room temperature, quenched with 30% acetic acid (5 mL) and most of the solvent removed under vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with water (3×10 mL), dried (MgSO4) and the solvent evaporated. The residue was chromatographed on silica gel with ethyl acetate to provide 0.11 g (yield 30%) of 5-[2-(9-phenyl-9H-fluoren-9-yl)ethyl]hydantoin as a white solid. 1H NMR (CD3OD, 300 MHz) δ: 7.79 (d, 2H), 7.40-7.00 (m, 11H), 3.86 (dd, 1 h), 2.75-2.50 (m, 2H), 1.98 (d, 1H), 1.35-0.8 (m, 3H); 13C NMR (CD3 0D, 75 MHz) δ: 177.8, 159.8, 152.3, 146.0, 142.1, 129.4, 128.9, 128.7, 127.6, 127.5, 125.4 121.1, 59.7, 59.4, 33.6, 27.8.

Workup

  1. customwas placed in a pressure tube
  2. temperatureThe reaction was then cooled to room temperature
  3. customquenched with 30% acetic acid (5 mL) and most of the solvent
  4. customremoved under vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  6. washwashed with water (3×10 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated
  9. customThe residue was chromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-afa40f01915d4808b56a734a34d5ff2d
Source dataset
uspto-grants-2000_12
Patent number
US06162824

Reaction notes

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