Pyridine → 2,3-Dichloro-6-(trifluoromethyl)benzonitrile
Reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:3]=1[C:4]([NH2:6])=O.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([C:12]([F:15])([F:13])[F:14])[C:3]=1[C:4]#[N:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 8.5 °C
Procedure
409 g of 2,3-dichloro-6-trifluoromethylbenzamide was dissolved in 2 liters of dioxane, and 263 g of pyridine was further added to the resultant solution. To this solution, 349 g of trifluoroacetic anhydride was added dropwise over 30 minutes while maintaining the temperature from 7 to 10° C. After stirring the solution for 2 hours at 25° C., the reaction mixture was poured into ice water. The precipitated crystals generated were then collected by filtration and were dissolved in ethyl acetate. The solution was then washed with water and saturated saline solution in series and dried over anhydrous magnesium sulfate. The solvent was distilled under reduced pressure, and the crude product obtained was washed with n-hexane and filtered to obtain 358 g of the title compound(mp. 53-54° C.).
Workup
- filtrationThe precipitated crystals generated were then collected by filtration
- dissolutionwere dissolved in ethyl acetate
- washThe solution was then washed with water and saturated saline solution in series
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled under reduced pressure
- customthe crude product obtained
- washwas washed with n-hexane
- filtrationfiltered
Sources & evidence
- ORD record
- ord-707c01b7418d493fa76e149db458bf4f
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06054605
Reaction notes
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