Acetic Acid → 4-[3-(1-Adamantyl)-4,5-methylenedioxyphenyl]-benzylidene-2,4-thiazolidinedione

関与物質

反応手順

A solution of toluene (100 mL), piperidine (100 μL), acetic acid (100 μL), 4-[3-(1-adamantyl)-4,5-methylenedioxyphenyl]-benzaldehyde (1.50 g, 4.16 mmol, see Example 1a) and 2-thioxo-4-thiazolidinone (0.554 g, 4.16 mmol) was heated at reflux overnight under an argon atmosphere. Within 20 minutes an orange-yellow solid formed. A Dean-Stark trap was attached and after 48 hours the reaction mixture was cooled to room temperature, and the resulting crystalline compound was filtered and washed with ethanol. The yellow solid was dried under high vacuum to afford 1.50 g (76%) of 4-[3-(1-adamantyl)-4,5-methylenedioxyphenyl]-benzylidene-2,4-thiazolidinedione, mp 337.5–338.5° (dec). 1H NMR (500 MHz; DMSO-d6): 1.75 (s, 6H), 2.05 (s, 9H), 6.05 (s, 2H), 7.07 (s, 1H), 7.22 (s, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.80 (d, J=8.0 Hz, 1H), 13.6–13.9 (brs, 1H).

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