Cesium carbonate → 4-(3,5-dichlorophenoxy)-3,5-dimethyl-1H-pyrazole
Reaction equation
Cl[CH:2]([C:6](=O)[CH3:7])[C:3](=O)[CH3:4].[Cl:9][C:10]1[CH:11]=[C:12]([OH:17])[CH:13]=[C:14]([Cl:16])[CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O.[NH2:25][NH2:26]>CC(C)=O>[Cl:9][C:10]1[CH:11]=[C:12]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[O:17][C:2]1[C:6]([CH3:7])=[N:25][NH:26][C:3]=1[CH3:4]Participants
6
Procedure
A mixture of 3-chloro-2,4-pentanedione (5.00 g, 37.0 mmol), 3,5-dichlorophenol (6.03 g, 37.0 mmol), caesium carbonate (12.0 g, 37.0 mmol) and acetone (40 ml) was heated at reflux for 18 hours. The mixture was cooled to room temperature, the solid was removed by filtration and the filtrate was evaporated under reduced pressure. The residue was dissolved in ethanol (30 ml) and hydrazine hydrate (1.85 g, 37.0 mmol) was added and the mixture was heated at 60° C. for 30 minutes. The mixture was concentrated under reduced pressure and the residue purified by chromatography on silica gel eluting with ethyl acetate in pentane (30:70) to give the title compound as a yellow solid (3.0 g).
Workup
- temperaturewas heated
- temperatureat reflux for 18 hours
- customthe solid was removed by filtration
- customthe filtrate was evaporated under reduced pressure
- dissolutionThe residue was dissolved in ethanol (30 ml)
- temperaturethe mixture was heated at 60° C. for 30 minutes
- concentrationThe mixture was concentrated under reduced pressure
- customthe residue purified by chromatography on silica gel eluting with ethyl acetate in pentane (30:70)
Sources & evidence
- ORD record
- ord-7098a789e48d448d8330052d56672728
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07157468B2
Reaction notes
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