Trifluoroacetic acid → N-[1-[1-(6-Chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoroacetamide
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]([F:14])([F:13])[C:10](O)=[O:11].P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[K+].[K+].[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33]Cl)=[CH:29][N:28]=1>C1(C)C=CC=CC=1.O.CN(C)C=O>[Cl:26][C:27]1[N:28]=[CH:29][C:30]([CH2:33][N:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]2=[N:1][C:10](=[O:11])[C:9]([F:14])([F:13])[F:8])=[CH:31][CH:32]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 5 °C
Procedure
In 10 ml of toluene, 1.0 g (10.6 mmol) of 2-aminopyridine was dissolved. After the solution was cooled to 5° C., 1.18 ml (15.9 mmol) of trifluoroacetic acid and 0.99 ml (10.6 mmol) of phosphorus oxychloride were added thereto, followed by stirring at room temperature for 6.5 hours. To the reaction liquid, 5.0 ml of dimethylformamide, 5.87 g (42.5 mmol) of potassium carbonate powder, and 1.72 g (10.6 mmol) of 2-chloro-5-chloromethylpyridine were added, and distillation was conducted under reduced pressure (60 to 35 hPa) at 50 to 60° C. Two and a half hours later, the reaction liquid was added to 100 ml of water, and the crystals were filtered, and washed with 30 ml of water and 15 ml of toluene. The obtained crystals were dried under reduced pressure at 60° C. Thus, 2.09 g of the target compound N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide was obtained (62.3%).
Workup
- additionwere added
- distillationdistillation
- customwas conducted under reduced pressure (60 to 35 hPa) at 50 to 60° C
- customTwo and a half hours later, the reaction liquid
- filtrationthe crystals were filtered
- washwashed with 30 ml of water and 15 ml of toluene
- customThe obtained crystals were dried under reduced pressure at 60° C
Sources & evidence
- ORD record
- ord-05a5546500bf4d9b94f0d48c14b69a2f
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09357776B2
Reaction notes
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