Sodium Acetate → HCID 86613930, compound

HRID 1811431Notes

Reaction equation

HRID 1811431 reaction equation
Cl[CH:2]([CH2:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:21])[N:13]2[CH3:20])[C:3]([OH:5])=O.[NH2:22][C:23](N)=[S:24].C([O-])(=[O:28])C.[Na+]>COC(O)C>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:8]([CH2:7][CH2:6][CH:2]2[S:24][C:23](=[O:28])[NH:22][C:3]2=[O:5])=[C:9]2[C:14]=1[N:13]([CH3:20])[C:12](=[O:21])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 86613911HCID 86613911, compound

Product 1

HCID 86613930HCID 86613930, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Conditions

Temperature
110 °C

Procedure

912 mg of 2-chloro-4-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)butyric acid, 390 mg of thiourea, and 394 mg of sodium acetate were added to 20 ml of methoxyethanol, followed by stirring at 110° C. for 4 hours. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and concentrated. The residue 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 recrystallized from a DMF-ethanol mixed solvent, giving 332 mg (31% yield) of 5-[2-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]thiazolidine-2,4-dione as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionThe residue was 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. customthe residue was recrystallized from a DMF-ethanol mixed solvent

Sources & evidence

ORD record
ord-799e2afb480c4766b44db392040a0bd3
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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