Potassium Carbonate → HCID 59165216, compound

HRID 1026375Notes

Reaction equation

HRID 1026375 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9](F)=[CH:8][CH:7]=1)=[O:5].[OH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>O.CO.C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:8][CH:7]=1)=[O:5]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 120399992,5-dichloro-4'-fluorobenzophenonHCID 178516071HCID 178516071, compound

Product 1

HCID 59165216HCID 59165216, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 22242641Methanol--water (1/1)Solvent

Procedure

Into a 2 L three-neck flask equipped with a stirrer, a thermometer, a cooling tube, a Dean-Stark tube, and a nitrogen-introducing three-way cock, 130.5 g (0.49 mol) of the above 2,5-dichloro-4′-fluorobenzophenone, 46.1 g (0.49 mol) of 2-hydroxypyridine, and 73.7 g (0.53 mol) of potassium carbonate were introduced. Then, 500 mL of N,N-dimethylacetamide (DMAc), and 100 mL of toluene were added, and in an oil bath, the mixture was heated under nitrogen atmosphere, and was reacted at 130° C. under stirring. Water resulting from the reaction was formed into an azeotropic mixture with toluene and was removed to the outside of the system through the Dean-Stark tube during the reaction. Approximately 3 hours thereafter, almost no water was recognized to be generated. Then, most of the toluene was removed, and the reaction was allowed to continue at 130° C. for 10 hours. A reaction liquid obtained was allowed to cool down, and then the reaction liquid was poured into 2 L of water/methanol (9/1). A product precipitated was filtered, and the filtrate was collected and dried. The dried product was introduced into a 2 L three-neck flask equipped with a stirrer, a thermometer, a cooling tube, a Dean-Stark tube, and a nitrogen-introducing three-way cock. The dried product was stirred in 1 L of toluene at 100° C., while the residual water content was distilled away, to thereby dissolve the dried product. After the solution was allowed to cool down, a crystallized product was filtered to thereby obtain an intended product of pale yellow, 2,5-dichloro-4′-(pyridine-2-oxy)benzophenone (30-2) in an amount of 142 g, and at an yield percentage of 83%.

Workup

  1. customInto a 2 L three-neck flask equipped with a stirrer
  2. additionwere introduced
  3. temperaturein an oil bath, the mixture was heated under nitrogen atmosphere
  4. customwas reacted at 130° C.
  5. customwas removed to the outside of the system through the Dean-Stark tube during the reaction
  6. customApproximately 3 hours
  7. customThen, most of the toluene was removed
  8. customA reaction liquid
  9. customobtained
  10. temperatureto cool down
  11. customthe reaction liquid
  12. customA product precipitated
  13. filtrationwas filtered
  14. customthe filtrate was collected
  15. customdried
  16. additionThe dried product was introduced into a 2 L three-neck flask
  17. customequipped with a stirrer
  18. additiona thermometer, a cooling tube, a Dean-Stark tube, and a nitrogen-introducing three-way cock
  19. stirringThe dried product was stirred in 1 L of toluene at 100° C., while the residual water content
  20. distillationwas distilled away
  21. dissolutionto thereby dissolve the dried product
  22. temperatureto cool down
  23. filtrationa crystallized product was filtered

Sources & evidence

ORD record
ord-31ce0461f0e347dbae2b16ae59120d06
Source dataset
uspto-grants-2014_05
Patent number
US08729219B2

Reaction notes

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