Thiazolidinedione → HCID 74348952, compound

Participants

Reaction Steps

4-Pyridin-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepine-7-carbaldehyde [compound of Example 1-Step III] (0.868 g, 3.4 mmol) was dissolved in 100 mL dry toluene and to this solution, was added 2,4-thiazolidinedione (0.402 g, 3.4 mmol) and piperidinium acetate (46 mg, 0.32 mmol). The reaction mixture was refluxed in a Dean Stark apparatus for 4 hours. The reaction mixture was cooled and filtered. The residue was washed with petroleum ether (500 mL) and dried in air to give crude material A (0.6 g). The filtrate and petroleum ether wash were combined, cooled overnight and filtered. The filtrate was washed with petroleum ether (500 mL). The residue was dried in air to give crude material B (0.24 g). Both crude materials, A and B were combined and purified by silica chromatography using 1% CH2Cl2 in MeOH to give 5-(4-pridin-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-7-ylmethylene)-thiazolidine-2,4-dione.

Provenance & Evidence