4-Hydroxybenzaldehyde → (5E)-5-[(4-Hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione

HRID 1868568Notes

Reaction equation

HRID 1868568 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>C(O)C>[CH:4]1[C:5](/[CH:6]=[C:14]2\[C:13]([NH:12][C:11]([S:10]\2)=[O:16])=[O:15])=[CH:8][CH:9]=[C:2]([OH:1])[CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 5437ThiazolidinedioneHCID 8082Piperidine

Product 1

HCID 1276528(5E)-5-[(4-Hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(Thiazolidin-2,4-dione-5-ylidinemethyl)-phenol (55) was synthesized by the condensation of 4-hydroxy benzaldehyde (53) with commercially available 2,4-thiazolidinedione (54) using piperidine as base in refluxing ethanol, according to a known procedure (Momose, Y.; Meguro, K.; Ikeda, H.; Hatanaka, C.; Oi, S.; Sohda, T. Chem. Pharm. Bull. 1991, 39, 1440.) (Scheme 5).

Sources & evidence

ORD record
ord-1609fca529b84a5fb2dffc4b615dcbbb
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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