4-Hydroxybenzaldehyde → HCID 3607913, compound

HRID 1648453Notes

Reaction equation

HRID 1648453 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 one 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 390 g of the title compound, melting at between 238° C. and 240° C.

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-e5d188d495b9403993c88af1c9496399
Source dataset
uspto-grants-1995_07
Patent number
US05436257

Reaction notes

Loading…