Potassium Carbonate → HCID 68659651, compound

HRID 2389225Notes

Reaction equation

HRID 2389225 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[SH:9].F[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>O>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:11][C:12]=1[S:9][C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 677943-FluoropyridineHCID 799652,5-Dichlorobenzenethiol

Product 1

HCID 68659651HCID 68659651, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

89.5 g (0.500 mol) of 2,5-dichlorobenzenethiol, 53.4 g (0.55 mol) of 3-fluoropyridine, 82.9 g (0.60 mol) of potassium carbonate, and 550 mL of anhydrous N,N′-dimethyl acetamide were weighed in a 2 L three-necked flask equipped with a stirrer, thermometer, cooling pipe, and nitrogen inlet tube. The reaction solution was heated to 100° C. for 3 hours under a nitrogen atmosphere using an oil bath. After confirming the disappearance of raw materials by way of thin-layer chromatography, the reaction liquid was allowed to cool to room temperature. Thereafter, the reaction liquid was gradually added to 3 L of water, and the product was solidified and filtered. The product obtained by filtering was dissolved in 2.5 L of toluene, and then washed with a sodium chloride solution using a separating funnel till the aqueous layer became neutral. The organic layer was dried using magnesium sulfate, and then the solvent was removed by an evaporator to obtain 2,5-dichlorophenyl pyridyl sulfide of an intermediate in an approximate yield amount of 129 g.

Workup

  1. customequipped with a stirrer
  2. temperaturethermometer, cooling pipe, and nitrogen inlet tube
  3. customthe reaction liquid
  4. temperatureto cool to room temperature
  5. customThereafter, the reaction liquid
  6. filtrationfiltered
  7. customThe product obtained
  8. filtrationby filtering
  9. dissolutionwas dissolved in 2.5 L of toluene
  10. washwashed with a sodium chloride solution
  11. customThe organic layer was dried
  12. customthe solvent was removed by an evaporator

Sources & evidence

ORD record
ord-7aeb44b6fe7a4618bd839388d8a0dab7
Source dataset
uspto-grants-2012_09
Patent number
US08273499B2

Reaction notes

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