Water → 2-Chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)benzaldehyde (O-methyl)oxime
Reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH3:7][O:8][N:9]=[CH:10][C:11]1[CH:16]=[C:15]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[NH:19][C:18]2=O)[C:14]([F:29])=[CH:13][C:12]=1[Cl:30].CI.O>CN(C)C=O>[CH3:7][O:8][N:9]=[CH:10][C:11]1[CH:16]=[C:15]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[N:19]([CH3:18])[C:1]2=[O:4])[C:14]([F:29])=[CH:13][C:12]=1[Cl:30]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
First, 117.1 g (0.85 mol) of potassium carbonate were added to a solution of 281.6 g (0.77 mol) of 2-chloro-4-fluoro-5-(6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)benzaldehyde (O-methyl)oxime in 0.8 l of dimethylformamide, whereupon a solution of 120.2 g of methyl iodide (0.85 mol) in 0.1 l of dimethylformamide was added dropwise in the course of 1 hour. The reaction mixture was subsequently stirred for 20 hours at approximately 20° C., and 0.9 l of water was subsequently added dropwise with ice-cooling. The product of value was extracted from the resulting solution using 1 l of dichloromethane. The extract was washed three times using 300 ml of water, dried over sodium sulfate and finally concentrated. Yield: 241 g; m.p.: 141-142° C. (diisopropyl ether).
Workup
- additionwas added dropwise in the course of 1 hour
- temperaturecooling
- extractionThe product of value was extracted from the resulting solution
- washThe extract was washed three times
- dry with materialdried over sodium sulfate
- concentrationfinally concentrated
Sources & evidence
- ORD record
- ord-c1987b6cbb9941a89a251d7d1c98961d
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06175007B1
Reaction notes
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