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

Temperature

90 °C

To sodium cyanide (0.425 g, 8.65 mmol) and ammonium carbonate (0.9 g, 11.54 mmol) in H2O (30 mL) was added 4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butyraldehyde (0.6 g, 2.88 mmol) in ethanol (30 mL). The black reaction mixture was heated to 90° C. After 1 h, the mixture became homogeneous and was stirred at 90° C. for 18 h. After cooling to 25° C., about 40 mL of solvent was removed in vacuo. Concentrated HCl (4 mL) was added to acidify the mixture to pH 1-2 and a precipitate formed. It was filtered. The mother liquor washed with EtOAc (3×50 mL). The organic layer was dried over MgSO4, filtered and concentrated to obtain 5-(3,3,3-trifluoro-1-(2,2,2-trifluoroethyl)propyl)imidazolidine-2,4-dione as a brown oil (1.01 g, 100%). Mass Spectrum (+ESI): 279, 280 (M+H)+.

1. customThe black reaction mixture
2. temperatureAfter cooling to 25° C.
3. customabout 40 mL of solvent was removed in vacuo
4. additionConcentrated HCl (4 mL) was added
5. customa precipitate formed
6. filtrationIt was filtered
7. washThe mother liquor washed with EtOAc (3×50 mL)
8. dry with materialThe organic layer was dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-40a62e2708854102b0305538901d0f6a

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547725B2