Sodium Hydroxide → 5-Cyclohexylmethylhydantoin

HRID 865377Notes

Reaction equation

HRID 865377 reaction equation
[OH-].[Na+].[CH:3]1([CH:9]=[C:10]2[NH:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4]1>[Pd]>[CH:3]1([CH2:9][CH:10]2[NH:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 573047295-(3-Cyclohexene-1-yl)methylenehydantoin

Product 1

HCID 118303575-CyclohexylmethylhydantoinYield 87.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
45 °C

Procedure

Twenty-five milliliters of a 5% aqueous sodium hydroxide solution, 3.84 g of 5-(3-cyclohexene-1-yl)methylenehydantoin and 0.43 g of wet 10% palladium on carbon (moisture 50%) were placed in a reactor equipped with a mechanical stirrer and a reflux condenser, and the mixture was reduced while stirring at 45° C. under a hydrogen pressure of 3.5 kg/cm2. After 9 hours, the palladium on carbon was removed by filtration, and the pH of the filtrate was adjusted to about 3 by addition of 1N hydrochloric acid, upon which white crystals were obtained. These were collected by filtration and washed with water, and then dried under reduced pressure at 60° C. overnight to obtain 3.43 g of 5-cyclohexylmethylhydantoin. The yield was 87.4%.

Workup

  1. customequipped with a mechanical stirrer and a reflux condenser
  2. customthe palladium on carbon was removed by filtration
  3. additionthe pH of the filtrate was adjusted to about 3 by addition of 1N hydrochloric acid, upon which white crystals
  4. customwere obtained
  5. filtrationThese were collected by filtration
  6. washwashed with water
  7. customdried under reduced pressure at 60° C. overnight

Sources & evidence

ORD record
ord-ef816d67dc394d66be7a0d80775964d4
Source dataset
uspto-grants-1996_10
Patent number
US05565575

Reaction notes

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