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

HRID 2199246Notes

Reaction equation

HRID 2199246 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]([F:16])([F:15])[C:10]([O:12]CC)=O.C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][N:25]=1>CN(C)C=O.O.CO.C1(C)C=CC=CC=1>[Cl:23][C:24]1[N:25]=[CH:26][C:27]([CH2:30][N:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]2=[N:1][C:10](=[O:12])[C:9]([F:8])([F:15])[F:16])=[CH:28][CH:29]=1

Participants

9

Reactant 4

HCID 9794Ethyl trifluoroacetateHCID 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 76.3%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

In 500 mL of dimethylformamide, 94 g (1 mol) of 2-aminopyridine was dissolved, and 284 g (2 mol) of ethyl trifluoroacetate was added thereto, followed by stirring at 55 to 60° C. for 24 hours. To the reaction liquid, 82.8 g (0.6 mol) of potassium carbonate powder, 153.9 g (0.95 mol) of 2-chloro-5-chloromethylpyridine, and 300 mL of toluene were added, followed by stirring under reduced pressure (36 hPa) at 50 to 60° C. for 3 hours. To the reaction liquid, 200 mL of methanol was added. Then, the reaction liquid was added to 2 L of hot water of 50° C. After being cooled to room temperature, the mixture was stirred for 3 hours. The crystals were filtered, and washed with 400 mL of water and 450 mL of toluene. The obtained crystals were dried under reduced pressure at 45° C. Thus, 228.9 g of the target compound was obtained (Percentage Yield: 72.7%).

Workup

  1. additionwere added
  2. stirringby stirring under reduced pressure (36 hPa) at 50 to 60° C. for 3 hours
  3. additionwas added
  4. customThen, the reaction liquid
  5. temperatureAfter being cooled to room temperature
  6. stirringthe mixture was stirred for 3 hours
  7. filtrationThe crystals were filtered
  8. washwashed with 400 mL of water and 450 mL of toluene
  9. customThe obtained crystals were dried under reduced pressure at 45° C

Sources & evidence

ORD record
ord-8d182a2b2f874352be0dd5aeb929df1d
Source dataset
uspto-grants-2016_06
Patent number
US09357776B2

Reaction notes

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