Thiazolidinedione → HCID 3607913, compound

HRID 1682764Notes

Reaction equation

HRID 1682764 reaction equation
O[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[S:10]1[CH2:14][C:13](=[O:15])[NH:12][C:11]1=[O:16].[C:17]([O-:20])(=[O:19])[CH3:18].[Na+].C(OC(=O)C)(=O)C>O.CC(N(C)C)=O>[C:17]([O:20][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[C:14]2[S:10][C:11](=[O:16])[NH:12][C:13]2=[O:15])=[CH:2][CH:9]=1)(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 5437ThiazolidinedioneHCID 6998SalicylaldehydeHCID 7918Acetic AnhydrideHCID 517045Sodium Acetate

Product 1

HCID 3607913HCID 3607913, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent2×

Procedure

A mixture comprising 200 g of -hydroxybenzaldehyde, 22 g of thiazolidine-2,4-dione, 280 g of sodium acetate and 660 ml of dimethylacetamide was stirred at 150° for 1 hour. It was then cooled, and 540 ml of dimethylacetamide and 370 ml of acetic anhydride were added to the reaction mixture. The resulting mixture was then stirred at 50° C. for 1.5 hours, after which it was poured into water. The solid which precipitated was collected by filtration, washed with water, and dried over anhydrous sodium sulfate, to give the title compound.

Workup

  1. temperatureIt was then cooled
  2. stirringThe resulting mixture was then stirred at 50° C. for 1.5 hours
  3. customThe solid which precipitated
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-27d4d1f0000346dab077e4fdde6da131
Source dataset
uspto-grants-1997_06
Patent number
US05635534

Reaction notes

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