4-Hydroxybenzaldehyde → HCID 3607913, compound

HRID 1901222Notes

Reaction equation

HRID 1901222 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[S:10]1[CH2:14][C:13](=[O:15])[NH:12][C:11]1=[O:16].[C:17]([O-])(=[O:19])[CH3:18].[Na+].C(OC(=O)C)(=O)C>O.CC(N(C)C)=O>[C:17]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:14]2[S:10][C:11](=[O:16])[NH:12][C:13]2=[O:15])=[CH:4][CH:3]=1)(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 5437ThiazolidinedioneHCID 7918Acetic AnhydrideHCID 517045Sodium Acetate

Product 1

HCID 3607913HCID 3607913, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent2×

Procedure

A mixture comprising 200 g of p-hydroxybenzaldehyde, 229 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-72e3b6c973394014ad61656902378351
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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