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

HRID 2217631Notes

Reaction equation

HRID 2217631 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(O)(=O)C1C=CC=CC=1.N1CCCCC1>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 243Benzoic AcidHCID 5437ThiazolidinedioneHCID 8082Piperidine

Product 1

HCID 5178225-((4-Hydroxyphenyl)methylene)-2,4-thiazolidinedioneYield 90.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 4-hydroxybenzaldehyde (3.67 g, 30 mmol), 2,4-thiazolidinedione (3.51 g, 30 mmol) and benzoic acid (4.40 g, 36 mmol) in toluene (100 mL) was added piperidine (4.5 mL, 45 mmol) and the mixture was equipped with a Dean Stark apparatus and brought to a vigorous reflux. After 45 min the mixture was cooled in an ice bath and the supernatant was decanted. The bright yellow solid was made into a suspension by the addition of glacial acetic acid (100 mL) and filtered through a Buchner funnel to yield a pale yellow solid (6.00 g, 90%). 1H NMR: (400 MHz, DMSO-d6): δ 12.45 (bs, 1H), 10.30 (s, 1H), 7.70 (s, 1H), 7.45 (d, J=8.8 Hz, 2H), 6.91 (d, J=8.8 Hz, 2H).

Workup

  1. customthe mixture was equipped with a Dean Stark apparatus
  2. temperatureAfter 45 min the mixture was cooled in an ice bath
  3. customthe supernatant was decanted
  4. additionThe bright yellow solid was made into a suspension by the addition of glacial acetic acid (100 mL)
  5. filtrationfiltered through a Buchner funnel

Sources & evidence

ORD record
ord-819cb864a39e407b8baca1b0ad5b71aa
Source dataset
uspto-grants-2008_08
Patent number
US07407978B2

Reaction notes

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