Toluene → 4-[3-(1-Adamantyl)-4-methoxyphenyl]benzylidene-2,4-thiazolidinedione

Participants

Reaction Steps

A solution of toluene (6 mL), piperidine (10 μL), acetic acid (10 μL), 4-[3-(1-adamantyl)-4-methoxyphenyl]benzaldehyde (0.337 g, 0.97 mmol) and 2,4-thiazolidinedione (0.114 g, 0.97 mmol) was heated at reflux overnight under an argon atmosphere. The reaction mixture was cooled to room temperature, and the resulting crystalline compound was filtered, washed with toluene and ethanol. The yellow solid was dried under high vacuum to afford 0.375 g (87%) of 4-[3-(1-adamantyl)-4-methoxyphenyl]benzylidene-2,4-thiazolidinedione, mp 304–306° C. 1H NMR (300 MHz; DMSO-d6): 1.75 (s, 6H), [2.06 (s), 2.11 (s), 9 H], 3.85 (s, 3H), 7.09 (d, J=8.7 Hz, 1H), 7.46 (d, J=2.3 Hz, 1H), 7.57 (dd, J=8.7 Hz, J=2.3 Hz, 1H), 7.65 (d, J=8.4 Hz, 2H), 7.80 (d, J=8.4 Hz, 2H), 7.82 (s, 1H), 12.4–12.7 (brs, 1H).

Provenance & Evidence