4-Hydroxybenzaldehyde → HCID 3607913, compound

HRID 1742503Notes

Reaction equation

HRID 1742503 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, compoundYield 90.5%

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 in vacuo, to give 390 g of 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. customdried in vacuo

Sources & evidence

ORD record
ord-364e16885d504be4b111d8b7517d5f13
Source dataset
uspto-grants-1994_08
Patent number
US05338855

Reaction notes

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