Water → 5-(3,3,3-Trifluoro-1-methylpropyl)imidazolidine-2,4-dione

HRID 1985924Notes

Reaction equation

HRID 1985924 reaction equation
[C-:1]#[N:2].[Na+].[C:4](=[O:7])([O-])[O-].[NH4+:8].[NH4+].[CH3:10][CH:11]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH:12]=O.[OH2:19]>C(O)C>[F:16][C:15]([F:18])([F:17])[CH2:14][CH:11]([CH:12]1[NH:8][C:1](=[O:19])[NH:2][C:4]1=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 517111Ammonium CarbonateHCID 743499924,4,4-Trifluoro-2-methylbutanal

Product 1

HCID 684293455-(3,3,3-Trifluoro-1-methylpropyl)imidazolidine-2,4-dioneYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To sodium cyanide (18.4 g, 375 mmol) and ammonium carbonate (39.0 g, 500 mmol) in H2O (450 mL) was added 2-methyl-4,4,4-trifluorobutanal (17.5 g, 125 mmol) in ethanol (450 mL). The reaction mixture was heated to 90° C. for 17 h. After cooling to 25° C., about 500 mL of solvent was removed in vacuo. Concentrated HCl was added to acidify the mixture to a pH of about 1 to about 2 and a precipitate formed. The mixture was filtered and washed with aqueous 1 N HCl to give 5-(3,3,3-trifluoro-1-methylpropyl)imidazolidine-2,4-dione as a white solid (15.5 g, 59%).

Workup

  1. temperatureAfter cooling to 25° C.
  2. customabout 500 mL of solvent was removed in vacuo
  3. additionConcentrated HCl was added
  4. customa precipitate formed
  5. filtrationThe mixture was filtered
  6. washwashed with aqueous 1 N HCl

Sources & evidence

ORD record
ord-9ab97389ff194c0c83d37164d427bc67
Source dataset
uspto-grants-2009_06
Patent number
US07547725B2

Reaction notes

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