Sodium Acetate → HCID 86613929, compound

HRID 504021Notes

Reaction equation

HRID 504021 reaction equation
Cl[CH:2]([CH2:6][C:7]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11](=[O:20])[N:12]2[CH3:19])[C:3]([OH:5])=O.[NH2:21][C:22](N)=[S:23].C([O-])(=[O:27])C.[Na+]>COC(O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:7]([CH2:6][CH:2]2[S:23][C:22](=[O:27])[NH:21][C:3]2=[O:5])=[C:8]2[C:13]=1[N:12]([CH3:19])[C:11](=[O:20])[CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 86613910HCID 86613910, compound

Product 1

HCID 86613929HCID 86613929, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Conditions

Temperature
110 °C

Procedure

1.0 g of 2-chloro-3-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)propionic acid, 0.45 g of thiourea, and 0.4 g of sodium acetate were added to 20 ml of methoxy ethanol, and the mixture was stirred at 110° C. for 7.5 hours. The reaction mixture was concentrated under reduced pressure, an aqueous sodium hydrogencarbonate solution was added to the residue to precipitate a solid, and the precipitated solid was collected by filtration. The filtrate was extracted with dichloromethane, and the extract was dried over anhydrous sodium sulfate and concentrated. The concentrated residue and the solid collected by filtration were combined and added to a mixed solvent of 10% hydrochloric acid and ethanol, followed by heating and refluxing overnight. The solvent was distilled off under reduced pressure, and the residue was recrystallized from an aqueous DMF, giving 0.41 g of 5-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-ylmethyl)thiazolidine-2,4-dione as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionan aqueous sodium hydrogencarbonate solution was added to the residue
  3. customto precipitate a solid
  4. filtrationthe precipitated solid was collected by filtration
  5. extractionThe filtrate was extracted with dichloromethane
  6. dry with materialthe extract was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. filtrationThe concentrated residue and the solid collected by filtration
  9. additionadded to a mixed solvent of 10% hydrochloric acid and ethanol
  10. temperatureby heating
  11. temperaturerefluxing overnight
  12. distillationThe solvent was distilled off under reduced pressure
  13. customthe residue was recrystallized from an aqueous DMF

Sources & evidence

ORD record
ord-f9851b9df7bb47d7be17e7320d56d76f
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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