Toluene → HCID 86586028, compound

Participants

Reaction Steps

A mixture of toluene (10 mL), piperidine (10 μL), acetic acid (10 μL), 6-[3-(1-adamantyl)-4,5-methylenedioxyphenyl]-2-naphthaldehyde (0.400 g, 0.974 mmol) and 2,4-thiazolidinedione (0.114 g, 0.974 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 0.344 g (69%) of 6-[3-(1-adamantyl)-4,5-methylenedioxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione, mp 304–306° (dec). 1H NMR (500 MHz; DMSO-d6): 1.76 (s, 6H), 2.07 (s, 9H), 6.06 (s, 2H), 7.16 (d, J=1.6 Hz, 1H), 7.29 (s, 1H), 7.68 (dd, J=1.0 Hz, J=9.0 Hz, 1H), 7.88 (d, J=9.0 Hz, 1H), 7.93 (s, 1H), 8.06 (d, J=9.0 Hz, 1H), 8.08 (d, J=8.8 Hz, 1H), 8.17 (s, 1H), 8.19 (s, 1H), 12.5–12.7 (brs, 1H).

Provenance & Evidence