Sodium Acetate → HCID 86613931, compound

HRID 1811432Notes

Reaction equation

HRID 1811432 reaction equation
Cl[CH:2]([CH2:6][CH2:7][CH2:8][C:9]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13](=[O:22])[N:14]2[CH3:21])[C:3]([OH:5])=O.[NH2:23][C:24](N)=[S:25].C([O-])(=[O:29])C.[Na+]>COC(O)C>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:9]([CH2:8][CH2:7][CH2:6][CH:2]2[S:25][C:24](=[O:29])[NH:23][C:3]2=[O:5])=[C:10]2[C:15]=1[N:14]([CH3:21])[C:13](=[O:22])[CH:12]=[CH:11]2

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 86613912HCID 86613912, compound

Product 1

HCID 86613931HCID 86613931, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Conditions

Temperature
110 °C

Procedure

1 g of 2-chloro-5-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)valeric acid, 380 mg of thiourea, and 380 mg of sodium acetate were added to 20 ml of methoxyethanol, followed by stirring at 110° C. for 5 hours. The reaction mixture was concentrated under reduced pressure, and water and a small amount of ethanol were added to the residue to precipitate a solid. The precipitated solid was collected by filtration. The solid collected by filtration was added to a mixed solvent of 10 ml of 10% hydrochloric acid and 10 ml of ethanol, followed by heating and refluxing overnight. The solvent was distilled off under reduced pressure, and the residue was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and concentrated. The concentrated residue was purified by silica gel column chromatography (dichloromethane:methanol of 100:1→10:1), and recrystallized from an ethanol-ether mixed solvent, giving 332 mg (29% yield) of 5-[3-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)propyl]thiazolidine-2,4-dione as a light yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  2. additiona small amount of ethanol were added to the residue
  3. customto precipitate a solid
  4. filtrationThe precipitated solid was collected by filtration
  5. filtrationThe solid collected by filtration
  6. additionwas added to a mixed solvent of 10 ml of 10% hydrochloric acid and 10 ml of ethanol
  7. temperatureby heating
  8. temperaturerefluxing overnight
  9. distillationThe solvent was distilled off under reduced pressure
  10. extractionthe residue was extracted with dichloromethane
  11. dry with materialThe extract was dried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. customThe concentrated residue was purified by silica gel column chromatography (dichloromethane:methanol of 100:1→10:1)
  14. customrecrystallized from an ethanol-ether mixed solvent

Sources & evidence

ORD record
ord-ce43ee8bbef648058a7a6aec89d9b9f9
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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