Reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:23]([C:24]2[N:28]([CH3:29])[N:27]=[C:26]([C:30]([CH3:32])=[O:31])[CH:25]=2)=[C:22]([Cl:33])[CH:21]=[CH:20][C:9]=1[C:10]([O:12]C1N(CC)N=CC=1)=O.O>O1CCOCC1>[Cl:7][C:8]1[C:23]([C:24]2[N:28]([CH3:29])[N:27]=[C:26]([C:30]([CH3:32])=[O:31])[CH:25]=2)=[C:22]([Cl:33])[CH:21]=[CH:20][C:9]=1[C:10]([C:25]1[CH:26]=[N:27][N:28]([CH2:24][CH3:23])[C:1]=1[OH:4])=[O:12]Participants
Procedure
0.076 g (0.6 mmol) of potassium carbonate was added to 0.16 g (0.4 mmol) of (1-ethylpyrazol-5-yl) 2,4-dichloro-3-(1-methyl-3-methylcarbonyl-1H-pyrazol-5-yl)benzoate in 3 ml of dioxane and the mixture was heated under reflux for 3 hours and then stirred at room temperature for 12 hours. 50 ml of water were added, the solution was washed with methylene chloride and methyl t-butyl ether, nitrogen was passed through and the pH was adjusted to 1 using 10% strength hydrochloric acid. The precipitate that had formed was filtered off with suction, washed with water and taken up in ethyl acetate. After drying, this organic phase was concentrated. 0.11 g (69% of theory) of 4-[2,4-dichloro-3-(1-methyl-3-methylcarbonyl-1H-pyrazol-5-yl)benzoyl]-1-ethyl-5-hydroxy-1H-pyrazole was obtained.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 3 hours
- washthe solution was washed with methylene chloride and methyl t-butyl ether, nitrogen
- customThe precipitate that had formed
- filtrationwas filtered off with suction
- washwashed with water
- customAfter drying
- concentrationthis organic phase was concentrated
Sources & evidence
- ORD record
- ord-e66cd86e9bf546feaafb03fc65e078f9
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06165944
Linked notes
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