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

HRID 341128Notes

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

Participants

Reactant 2

HCID 1264-Hydroxybenzaldehyde

HCID 5437Thiazolidinedione

Product 1

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

Procedure

A compounds of Formula 3A can be synthesized according to Scheme 1A, wherein 4-hydroxybenzaldehyde is condensed with thiazolidine-2,4-dione under Knoevenagel conditions to produce (E)-5-(4-hydroxybenzylidene)thiazolidine-2,4-dione. This intermediate can then be reduced to the compound of Formula 3A by, for example, hydrogenation.

Sources & evidence

ORD record: ord-78161dd76cc94020a9c52df652892faa
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895748B2

Reaction notes

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