Potassium Phosphate, Tribasic → HCID 67313208, compound

HRID 2092200Notes

Reaction equation

HRID 2092200 reaction equation
I[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[N+:12]([O-:14])=[O:13].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:23][C:24]1[CH:25]=[C:26](S)[CH:27]=[CH:28][CH:29]=1.O.O.O.O.O.O.[Mg+2].C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=O.[S:51](S([O-])=O)([O-:54])(=O)=[O:52].[Na+].[Na+]>C(O)CO.ClCCl.CO>[F:23][C:24]1[CH:29]=[C:28]([S:51]([C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][C:6]=3[N+:12]([O-:14])=[O:13])(=[O:54])=[O:52])[CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 75710m-FluorobenzenethiolHCID 656671Sodium PyrosulfiteHCID 120323673-Iodo-8-nitroquinolineHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)

Product 1

HCID 67313208HCID 67313208, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
80 °C

Procedure

15 g of 3-iodo-8-nitroquinoline (50 mmol), 0.476 g CuJ (2.5 mmol) and 21.22 g K3PO4 (100 mmol) were suspended in 150 ml of ethylene glycol. 9.61 g 3-fluorobenzenethiol were added and the reaction mixture was stirred at 80° C. for 6 h followed by stirring for 14 h at room temperature. The reaction mixture was partitioned between 150 ml of dichloromethane and 150 ml of water, and after stirring for 15 min, the organic phase was separated. The aqueous layer was extracted one more time with dichloromethane, the combined organic layers were washed with water and stirred with 5 g charcoal for 15 min. The filtrate was added to a suspension of 54.1 g (87 mmol) monoperoxy-phthalic acid magnesium salt hexahydrate in 300 ml of dichloromethane/methanol at 10-25° C. within 30 min. After stirring for 16 h at room temperature, the reaction mixture was cooled and slowly 250 mL of an aqueous sodium pyrosulfite solution were added. The organic phase and the precipitate were separated and washed with 250 ml of aqueous sodium bicarbonate solution. After stirring for 15 min, the precipitate was filtered, washed with water and ether, and dried under vacuum to yield 11.7 g of the product.

Workup

  1. stirringby stirring for 14 h at room temperature
  2. customThe reaction mixture was partitioned between 150 ml of dichloromethane and 150 ml of water
  3. stirringafter stirring for 15 min
  4. customthe organic phase was separated
  5. extractionThe aqueous layer was extracted one more time with dichloromethane
  6. washthe combined organic layers were washed with water
  7. stirringstirred with 5 g charcoal for 15 min
  8. stirringAfter stirring for 16 h at room temperature
  9. temperaturethe reaction mixture was cooled
  10. customThe organic phase and the precipitate were separated
  11. washwashed with 250 ml of aqueous sodium bicarbonate solution
  12. stirringAfter stirring for 15 min
  13. filtrationthe precipitate was filtered
  14. washwashed with water and ether
  15. customdried under vacuum

Sources & evidence

ORD record
ord-7f79fdf7962f428892af5b95e1d65dc4
Source dataset
uspto-grants-2013_05
Patent number
US08440694B2

Reaction notes

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