Water → 5-Methyl-5-phenylhydantoin

HRID 744915Notes

Reaction equation

HRID 744915 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[C-:10]#[N:11].[Na+].[C:13](=[O:16])(O)[O-].[NH4+:17].[OH2:18]>>[CH3:2][C:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:17][C:10](=[O:18])[NH:11][C:13]1=[O:16]

Participants

5

Reactant 4

HCID 962WaterHCID 7410AcetophenoneHCID 8929Sodium CyanideHCID 14013Ammonium Bicarbonate

Product 1

HCID 930435-Methyl-5-phenylhydantoin

Procedure

30 g of acetophenone diluted in 250 ml of 95° alcohol are added over 30 minutes to a mixture of 18.35 g of sodium cyanide and 125 g of ammonium bicarbonate in 250 ml of water and the reaction medium is heated at 60°-65° C. for 22 hours, with stirring. It is concentrated to half its volume under vacuum and the solid which has precipitated is filtered off, washed with water and ether and then dried under vacuum to give 38 g of a white solid, which is identified by IR.

Workup

  1. temperaturethe reaction medium is heated at 60°-65° C. for 22 hours
  2. concentrationIt is concentrated to half its volume under vacuum
  3. customthe solid which has precipitated
  4. filtrationis filtered off
  5. washwashed with water and ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-fdce0d827d4d4686b91cb225a3887b4d
Source dataset
uspto-grants-1996_09
Patent number
US05559233

Reaction notes

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