Benzoic Acid → HCID 86589683, compound

Participants

Reaction Steps

In a 100 mL round-bottomed flask equipped with a Dean-Stark apparatus, a mixture of 45 (1.55 g, 4.2 mmol), 2,4-thiazolidinedione (0.5 g, 4.2 mmol), benzoic acid (0.62 g, 5.0 mmol) and piperidine (0.62 mL, 6.3 mmol) was azeotroped in toluene (60 mL) for 45 min under vigorous reflux. The reaction mixture was cooled then poured over 10% citric acid (40 mL) and stirred until a bright yellow solid formed. The solid was filtered and washed with water and the wet solid was azeotroped and recrystallized from toluene to yield 1.83 g (93%) of 46. 1H NMR (400 MHz, DMSO-d6): δ 12.72 (br s, 1H), 12.57 (br s, 1H), 7.77 (s, 1H), 7.70 (s, 1H), 7.63 (d, J=8.8 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H), 7.14 (d, J=8.4 Hz, 2H), 7.12 (d, J=8.8 Hz, 2H), 6.92 (s, 1H), 6.69 (s, 2H), 2.16 (s, 6H).

Provenance & Evidence