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
- 80 °C
Procedure
A mixture of α-trifluoromethylacrylic acid (350 mg; 2.5 mmoles), urea (162 mg; 2.7 mmoles) and acetic anhydride (2 ml) was heated at 80° C. with stirring for 2 hours. After cooling to 0° C., the precipitated white solid was filtered off to give 210 mg (yield: 46%) of 5-trifluoromethyldihydrouracil. The solvent was evaporated under reduced pressure from the filtrate. The residue was crystallized from ethanol to give additional 95 mg (yield: 21%) of the above product. The total yield was 67%.
Workup
- temperatureAfter cooling to 0° C.
- filtrationthe precipitated white solid was filtered off
Sources & evidence
- ORD record
- ord-c850cea8223043b7a6829418cdb1aff5
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04581452
Reaction notes
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