Benzoic Acid → (E)-Methyl 4-(2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)ethoxy)benzoate

Participants

Reaction Steps

To a solution of 355 (1.59 g, 3.86 mmol) in toluene (10 mL) was added thiazolidine-2,4-dione (542 mg, 4.63 mmol), benzoic acid (61.3 mg, 0.50 mmol) and piperidine (57 μL, 0.58 mmol). The resultant mixture was refluxed with the Dean-Stark adapter for ½ h and cooled to the room temperature. A precipitate formed which was collected by filtration to afford the title compound (1.41 g, 92%). 1H NMR: (DMSO-d6) δ (ppm): 7.90 (d, J=8.8 Hz, 2H), 7.73 (s, 1H), 7.54 (d, J=8.8 Hz, 2H), 7.14 (d, J=8.8 Hz, 2H), 7.08 (d J=8.8 Hz, 2H), 4.42 (bs, 4H), 3.80 (s, 3H). LRMS (ESI): (calc.) 399.1; (found) 400.0 (MH)+.

Provenance & Evidence