Potassium Carbonate → 2-chloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2-difluoroacetamide

HRID 2199261Notes

Reaction equation

HRID 2199261 reaction equation
[Cl:1][C:2]([F:13])([F:12])[C:3]([N:5]=[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][NH:7]1)=[O:4].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Cl)=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]([F:12])([F:13])[C:3]([N:5]=[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]1[CH2:21][C:18]1[CH:17]=[N:16][C:15]([Cl:14])=[CH:20][CH:19]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 178522124HCID 178522124, compound

Product 1

HCID 866869322-chloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2-difluoroacetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 68 mg (0.33 mmol) of 2-chloro-2, 2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide synthesized by the above-described method, 53 mg (0.33 mmol) of 2-chloro-5-chloromethylpyridine dissolved in 6 ml of anhydrous acetonitrile was added. Subsequently, 50 mg (0.36 mmol) of potassium carbonate was added to the mixture, followed by heating under reflux for 1 hour. After completion of the reaction, the reaction liquid was returned to room temperature, and then concentrated under reduced pressure. Diethyl ether was added to the residue. As a result, a solid was precipitated. The solid was collected by filtration, and dried. Thus, the target substance was obtained. Yield: 49 mg (Percentage Yield: 45%).

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperatureunder reflux for 1 hour
  4. customAfter completion of the reaction
  5. customthe reaction liquid
  6. customwas returned to room temperature
  7. concentrationconcentrated under reduced pressure
  8. additionDiethyl ether was added to the residue
  9. customAs a result, a solid was precipitated
  10. filtrationThe solid was collected by filtration
  11. customdried
  12. customThus, the target substance was obtained

Sources & evidence

ORD record
ord-595778617f7747d8a8d733e8ed6ec51d
Source dataset
uspto-grants-2016_06
Patent number
US09357776B2

Reaction notes

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