N,N-Diethylaniline → HCID 15477207, compound
Reaction equation
C(N(CC)[C:4]1[CH:9]=CC=C[CH:5]=1)C.[Cl:12][C:13]1[CH:18]=[C:17]([O:19]CC#C)[C:16]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[N:25]([CH3:34])[C:24]2=[O:35])=[C:15]([F:36])[CH:14]=1.[F-].[Cs+]>O>[Cl:12][C:13]1[C:18]2[CH:5]=[C:4]([CH3:9])[O:19][C:17]=2[C:16]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:31])([F:33])[F:32])[N:25]([CH3:34])[C:24]2=[O:35])=[C:15]([F:36])[CH:14]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 185 °C
Procedure
100 ml of N,N-diethylaniline was added to 5.2 g (14 mmol) of 3-(4-chloro-2-fluoro-6-propargyloxyphenyl)-1-methyl-6-trifluoromethyluracil and 6.4 g (42 mmol) of cesium fluoride, followed by stirring at 180 to 190° C. for 3 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution, water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 1.4 g (yield: 26.9%) of the desired product as white powder. Melting point: 196-197° C.
Workup
- customAfter completion of the reaction
- extractionextracted with ethyl acetate
- washThe organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution, water
- dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customThen, the obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-ae201e23373348418dfeb5a7f2129cc7
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06130187
Reaction notes
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