2-Chlorobenzoic Acid → HCID 12226008, compound

HRID 918196Notes

Reaction equation

HRID 918196 reaction equation
[K].Cl[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[F:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.[C:20](=O)([O-])[O-:21].[K+].[K+]>[Cu].CN(C)C=O>[F:12][C:13]1[CH:19]=[CH:18][C:16]([N:17]2[C:20](=[O:21])[O:7][C:5](=[O:6])[C:4]3=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]23)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 83742-Chlorobenzoic AcidHCID 97314-FluoroanilineHCID 11430Potassium CarbonateHCID 5462222Potassium

Product 1

HCID 12226008HCID 12226008, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

The potassium salt of o-chlorobenzoic acid (25 g), 25 g. of 4-fluoroaniline, 9 g. potassium carbonate and 2 g. of copper powder were heated under reflux in 200 ml. dimethylformamide. After cooling the solvent was evaporated, the residue dissolved in 500 ml. of absolute ethanol, the solution was filtered and the filtrate evaporated. The residue was suspended in 300 ml. of methylene chloride and filtered. The solid (on 10 filter) was dissolved in 100 ml. of water and 45 g. of potassium carbonate was added. To this solution 65 ml. phosgene (12.5% in benzene) was added under vigorous stirring. The stirring was continued for 18 hours at room temperature. The precipitate, which had formed, was filtered off and washed with water. After air drying the filter case was dissolved in chloroform (200 ml.) and the solution treated with solid sodium carbonate, aluminium oxide and activated charcoal. The solvent was then exchanged for ether and the material, which crystallized, was collected by filtration, m.p. 199°-201°.

Workup

  1. temperatureunder reflux in 200 ml
  2. temperatureAfter cooling the solvent
  3. customwas evaporated
  4. dissolutionthe residue dissolved in 500 ml
  5. filtrationof absolute ethanol, the solution was filtered
  6. customthe filtrate evaporated
  7. filtrationof methylene chloride and filtered
  8. filtrationThe solid (on 10 filter)
  9. dissolutionwas dissolved in 100 ml
  10. additionof potassium carbonate was added
  11. additionphosgene (12.5% in benzene) was added under vigorous stirring
  12. customThe precipitate, which had formed
  13. filtrationwas filtered off
  14. washwashed with water
  15. customAfter air drying the filter case
  16. dissolutionwas dissolved in chloroform (200 ml.)
  17. additionthe solution treated with solid sodium carbonate, aluminium oxide and activated charcoal
  18. customthe material, which crystallized
  19. filtrationwas collected by filtration, m.p. 199°-201°

Sources & evidence

ORD record
ord-0534e3a718dc4bfeb47be098a54f4919
Source dataset
uspto-grants-1976_07
Patent number
US03969506

Reaction notes

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