Acetonitrile → HCID 54515861, compound

HRID 520759Notes

Reaction equation

HRID 520759 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:16][C:17]([F:27])([F:26])[C:18](=[O:25])[CH:19]=[C:20]1C[CH2:23][CH2:22][S:21]1.C(#[N:30])C>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:30]2[CH2:23][CH2:22][S:21][C:20]2=[CH:19][C:18](=[O:25])[C:17]([F:27])([F:26])[F:16])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 86686935HCID 86686935, compound

Product 1

HCID 54515861HCID 54515861, compoundYield 50%

Procedure

2-chloro-5-chloromethylpyridine (80 mg, 0.50 mmol) dissolved in 8 mL of anhydrous acetonitrile, and potassium carbonate (69 mg, 0.50 mmol) were added to 65 mg (0.33 mmol) of 1,1,1-trifluoro-3-(thiaolidin-2-ylidene)propane-2-one obtained by the foregoing method, and the mixture was refluxed under heating for 2 hours. After reaction completion, the reaction mixture was returned to room temperature, insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=1:1→1:3), giving 53 mg of the target compound (yield, 50%).

Workup

  1. customobtained by the foregoing method
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 2 hours
  4. customAfter reaction completion
  5. customwas returned to room temperature
  6. custominsoluble matter was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=1:1→1:3)

Sources & evidence

ORD record
ord-43e54bcab72e433aa07f08340d2613b9
Source dataset
uspto-grants-2016_05
Patent number
US09328068B2

Reaction notes

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