Urea → 5-(Trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dione
Reaction equation
[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4](O)=[O:5].[NH2:10][C:11]([NH2:13])=[O:12].C(OC(=O)C)(=O)C>>[F:1][C:2]([F:9])([F:8])[CH:3]1[CH2:7][NH:13][C:11](=[O:12])[NH:10][C:4]1=[O:5]Participants
4
Conditions
- Temperature
- 100 °C
Procedure
A mixture of α-trifluoromethylacrylic acid (700 mg; 5 mmoles), urea (300 mg; 5 mmoles) and acetic anhydride (2 ml) was heated at 100° C. with stirring for 1 hour. After cooling to 0° C., the precipitated solid was filtered off to give 450 mg (yield: 40%) of 5-trifluoromethyl-5,6-dihydrouracil. The solvent was evaporated under reduced pressure from the filtrate, and the residue was recrystallized from ethanol to give additional 160 mg (yield: 27%) of 5-trifluoromethyl-5,6-dihydrouracil. The total yield of the product was 67%.
Workup
- temperatureAfter cooling to 0° C.
- filtrationthe precipitated solid was filtered off
Sources & evidence
- ORD record
- ord-f7e1dbbe470c45618e1ab5f44c1bbd52
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04581452
Reaction notes
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