4-Hydroxybenzaldehyde → 5-((4-Hydroxyphenyl)methylene)-2,4-thiazolidinedione

HRID 1009186

Reaction equation

HRID 1009186 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].N1CCCCC1.CC(O)=O>C1(C)C=CC=CC=1>[OH: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

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082Piperidine

Product 1

HCID 5178225-((4-Hydroxyphenyl)methylene)-2,4-thiazolidinedioneYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of p-hydroxybenzaldehyde (vi; 0.5 mmol), 2,4-thiazolidinedione, (0.6 mmol), and catalytic amounts of piperidine and AcOH was refluxed in toluene (5 mL) for 24 h. The precipitated product was filtered, washed with toluene (3×10 mL), and dried in vacuo at 60° C. overnight, yielding 5-(4-hydroxybenzylidene)-thiazolidine-2,4-dione (vii) in a 85% yield.

Workup

  1. filtrationThe precipitated product was filtered
  2. washwashed with toluene (3×10 mL)
  3. customdried in vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-055cc3d325ae41eb8eb284ffa6a4fd0d
Source dataset
uspto-grants-2011_07
Patent number
US07973062B2

Linked notes

Loading…