Trifluoroacetic acid → N-[1-[1-(6-Chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoroacetamide

HRID 2199257Notes

Reaction equation

HRID 2199257 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].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Cl)=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(C)=CC=CC=1.O.CO.CN(C)C=O>[Cl:15][C:16]1[N:17]=[CH:18][C:19]([CH2:22][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:20][CH:21]=1

Participants

9

Reactant 4

HCID 6422Trifluoroacetic acidHCID 104392-AminopyridineHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 14127920N-[1-[1-(6-Chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoroacetamideYield 80,081.5%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
150 °C

Procedure

In 40 ml of xylene, 2.35 g (0.025 mol) of 2-aminopyridine was suspended. To this mixture, 2.85 g (0.025 mmol) of trifluoroacetic acid and 135 mg of ferric chloride hexahydrate were added, and attached a Dean-Stark trap. The mixture was stirred at 150° C. for 16 hours, removing the resulting water by the Dean-Stark trap. After the solution was cooled to 60° C., 4.05 g (0.025 mol) of 2-chloro-5-chloromethylpyridine, 16 mL of dimethylformamide, and 2.42 g (0.0175 mol) of potassium carbonate were added, followed by stirring under a reduced pressure of 60-110 hPa at 60 to 65° C. for 3 hours. Then, 10 mL of methanol was added to the reaction mixture, and this mixture was added to 80 mL of hot water of 50° C. The mixture was cooled to room temperature with stirring. Crystals were filtered, and washed with 20 mL of water and 20 mL of toluene. The obtained crystals were dried under reduced pressure at 60° C. Thus, 6.32 g of the target compound was obtained (Percentage Yield: 80.3%).

Workup

  1. customremoving the resulting water by the Dean-Stark trap
  2. temperatureAfter the solution was cooled to 60° C.
  3. stirringby stirring under a reduced pressure of 60-110 hPa at 60 to 65° C. for 3 hours
  4. temperatureThe mixture was cooled to room temperature
  5. stirringwith stirring
  6. filtrationCrystals were filtered
  7. washwashed with 20 mL of water and 20 mL of toluene
  8. customThe obtained crystals were dried under reduced pressure at 60° C

Sources & evidence

ORD record
ord-1f25037dc1c948fd8d1ede6bb2df19f0
Source dataset
uspto-grants-2016_06
Patent number
US09357776B2

Reaction notes

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