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

HRID 1157985Notes

Reaction equation

HRID 1157985 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.CO>C(O)(=O)C.O>[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

7

Reactant 4

HCID 1264-Hydroxybenzaldehyde2×HCID 887MethanolHCID 5437Thiazolidinedione2×HCID 8082Piperidine

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 4-hydroxy benzaldehyde, 36 (3 g, 24.6 mmol), 2,4-thiazolidinedione, 37 (2.9 g, 24.8 mmol), piperidine (2.5 mL) and methanol (100 mL) was refluxed for 18 h. The reaction mixture was poured into water and acidified with acetic acid to give 38, which was recrystallised from methanol. Yield 4.7 g (86%); mp 296-298° C.; MS (FAB) 222 (M++1); IR (KBr) 3404, 3123, 1723, 1678; 1H NMR (200 MHz, DMSO-d6) δ 7.70 (s, 1H), 7.46 (d, J=8.6 Hz, 2H), 6.93 (d, J=8.6 Hz, 2H).

Workup

  1. temperaturewas refluxed for 18 h

Sources & evidence

ORD record
ord-86bd44a3b7fc4e1399930d3d4ee1ebad
Source dataset
uspto-grants-2010_10
Patent number
US07807712B2

Reaction notes

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