Sodium Acetate → HCID 86613932, compound

HRID 1811433Notes

Reaction equation

HRID 1811433 reaction equation
Cl[CH:2]([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]([O:5]CC)=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]([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 86613933HCID 86613933, compound

Product 1

HCID 86613932HCID 86613932, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Conditions

Temperature
110 °C

Procedure

3.02 g of ethyl chloro-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)acetate, 1.4 g of thiourea, and 2 g of sodium acetate were added to 50 ml of methoxyethanol, followed by stirring at 110° C. for 2.5 hours. The reaction mixture was concentrated under reduced pressure. Water was added to the residue to precipitate a solid, and the precipitated solid was collected by filtration. The collected solid was added to a mixed solvent of 30 ml of 10% hydrochloric acid and 30 ml of ethanol, followed by heating and refluxing overnight. The resultant was concentrated to half its original volume under reduced pressure. Water was added thereto, and the mixture was cooled with ice to precipitate a solid. The precipitated solid was collected by filtration. The solid was recrystallized from a DMF-ethanol mixed solvent, giving 1.68 g (57% yield) of 5-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)thiazolidine-2,4-dione as a gray powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. customto precipitate a solid
  4. filtrationthe precipitated solid was collected by filtration
  5. additionThe collected solid was added to a mixed solvent of 30 ml of 10% hydrochloric acid and 30 ml of ethanol
  6. temperatureby heating
  7. temperaturerefluxing overnight
  8. concentrationThe resultant was concentrated to half its original volume under reduced pressure
  9. additionWater was added
  10. temperaturethe mixture was cooled with ice
  11. customto precipitate a solid
  12. filtrationThe precipitated solid was collected by filtration
  13. customThe solid was recrystallized from a DMF-ethanol mixed solvent

Sources & evidence

ORD record
ord-8f5adcd3f47c4aa9a90eaeba696063e6
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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