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

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).

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)

ORD record

ord-58eeeba76a1440f99f30644d56ea0ce2

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07718682B2