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].C1CCC(N=C=NC2CCCCC2)CC1>CN(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
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of α-trifluoromethylacrylic acid (700 mg; 5.0 mmoles) and urea (318 mg; 5.3 mmoles) in DMF (5 ml) was heated at 90° C. with stirring for 5 hours. After cooling to 0° C., a solution of DCC (1.09 g; 5.3 mmoles) in DMF (3 ml) was added dropwise. The mixture was stirred for 1 hour, and the precipitated solid was filtered off and washed with ethyl acetate. The solvents were evaporated under reduced pressure from the combined filtrates. The residue was purified by a column chromatography on silica gel (ethyl acetate) to give 382 mg (yield: 42%) of 5-trifluoromethyl-5,6-dihydrouracil. m.p.: 203°-205° C. (dec.) [value reported in the literature 203°-205° C. (dec.)].
Workup
- temperatureAfter cooling to 0° C.
- stirringThe mixture was stirred for 1 hour
- filtrationthe precipitated solid was filtered off
- washwashed with ethyl acetate
- customThe solvents were evaporated under reduced pressure from the combined filtrates
- customThe residue was purified by a column chromatography on silica gel (ethyl acetate)
Sources & evidence
- ORD record
- ord-c5bbc0d1f2db4e48a6a5f6f7e3339f6c
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04581452
Reaction notes
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