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

HRID 1868607Notes

Reaction equation

HRID 1868607 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].CO.O>C(O)(=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

6

Reactant 4

HCID 1264-Hydroxybenzaldehyde2×HCID 887MethanolHCID 962WaterHCID 5437Thiazolidinedione2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-hydroxy benzaldehyde, 53 (3 g, 24.6 mmol), 2,4-thiazolidinedione, 54 (2.9 g, 24.8 mmol), pipieridine (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 55, 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-da40fd71646040c4a9bd77f2cba17a0c
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

Loading…