Benzoic Acid → 5-[4-(4'-Methoxybiphenyl-3-yloxy)-benzylidene]-thiazolidine-2,4-dione

HRID 2217638Notes

Reaction equation

HRID 2217638 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)[CH:10]=2)=[CH:5][CH:4]=1.[S:24]1[CH2:28][C:27](=[O:29])[NH:26][C:25]1=[O:30].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[C:28]4[S:24][C:25](=[O:30])[NH:26][C:27]4=[O:29])=[CH:18][CH:17]=3)[CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 593029604-(4'-Methoxybiphenyl-3-yloxy)-benzaldehyde

Product 1

HCID 853403575-[4-(4'-Methoxybiphenyl-3-yloxy)-benzylidene]-thiazolidine-2,4-dioneYield 77.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 57 (1.23 g, 4.0 mmol), 2,4-thiazolidinedione (0.48 g, 4.0 mmol), benzoic acid (0.60 g, 4.8 mmol) and piperidine (0.61 mL, 6.0 mmol) in toluene (30 mL) was heated to a vigorous reflux until most of the solvent had evaporated. A yellow suspension was achieved by addition of acetic acid (25 mL) followed by sonication. Filtration of the suspension followed by washing with acetic acid (10 mL) yielded 58 (1.25 g, 75%) after filtration and oven drying. 1H NMR (400 MHz, DMSO-d6): δ 12.57 (br s, 1H), 7.78 (s, 1H), 7.63 (d, J=8.8 Hz, 2H), 7.62 (d, J=8.8 Hz, 2H), 7.49 (d, J=5.2 Hz, 2H), 7.36 (t, J=1.6 Hz, 1H), 7.16 (d, J=8.8 Hz, 2H), 7.03 (m, 1H), 7.01 (d, J=8.8 Hz, 2H), 3.7 (s, 3H).

Workup

  1. temperaturewas heated to
  2. temperaturea vigorous reflux until most of the solvent
  3. customhad evaporated
  4. additionA yellow suspension was achieved by addition of acetic acid (25 mL)
  5. customfollowed by sonication
  6. filtrationFiltration of the suspension
  7. washby washing with acetic acid (10 mL)

Sources & evidence

ORD record
ord-166605d53bd54cb3a60b8af865b3aa6b
Source dataset
uspto-grants-2008_08
Patent number
US07407978B2

Reaction notes

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