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

HRID 2199251Notes

Reaction equation

HRID 2199251 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.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.CO>[Cl:17][C:18]1[N:19]=[CH:20][C:21]([CH2:24][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:22][CH:23]=1

Participants

8

Reactant 4

HCID 9794Ethyl trifluoroacetate2×HCID 104392-AminopyridineHCID 11430Potassium Carbonate2×HCID 1554792-Chloro-5-(chloromethyl)pyridine2×

Product 1

HCID 14127920N-[1-[1-(6-Chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoroacetamideYield 76%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

In 50 mL of dimethylformamide, 9.4 g (0.1 mol) of 2-aminopyridine was dissolved. To this solution, 28.8 g (0.2 mol) of ethyl trifluoroacetate, 16.2 g (0.1 mol) of 2-chloro-5-chloromethylpyridine, and 13.8 g (0.1 mol) of potassium carbonate were added, followed by stirring at 55 to 60° C. for 20 hours. To the reaction liquid, 1.38 g (0.1 mol) of potassium carbonate powder, 3.24(0.02 mol) of 2-chloro-5-chloromethylpyridine, and 5.68 g (0.04 mol) of ethyl trifluoroacetate were further added, followed by stirring at 55 to 60° C. for 6 hours. To the reaction liquid, 40 mL of methanol was added, and then the reaction liquid was added to 300 mL of hot water of 50° C. After being cooled to room temperature, the mixture was stirred for 1 hour. The crystals were filtered, and washed with 100 mL of water and 75 mL of toluene. The obtained crystals were dried under reduced pressure at 45° C. Thus, 24.0 g of the target compound was obtained (Percentage Yield: 76%).

Workup

  1. additionwere further added
  2. stirringby stirring at 55 to 60° C. for 6 hours
  3. additionwas added
  4. customthe reaction liquid
  5. temperatureAfter being cooled to room temperature
  6. stirringthe mixture was stirred for 1 hour
  7. filtrationThe crystals were filtered
  8. washwashed with 100 mL of water and 75 mL of toluene
  9. customThe obtained crystals were dried under reduced pressure at 45° C

Sources & evidence

ORD record
ord-d79ae5c387374c5a991c4cc5a9350f96
Source dataset
uspto-grants-2016_06
Patent number
US09357776B2

Reaction notes

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