Thiazolidinedione → 5-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-benzylidene]-thiazolidine-2,4-dione

Participants

Reaction Steps

A mixture of 4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzaldehyde benzaldehyde (Taylor, E. C., Skotnicki, J. S. Synthesis, 1981, 606) (15 g, 60 mol), 2,4-thiazolidinedione (7.0 g, 60 mmol), and piperidine (8.0 mL, 81.2 mmol) in 450 mL of ethanol was refluxed for 6 hours. The solid which was formed on cooling the solution was collected to give the title compound as an orange solid (20.5 g, 99%); 1H NMR (300 MHz, DMSO-d6) δ 1.67 (t, J=5.6 Hz, 4 H), 3.47 (t, J=5.6 Hz, 4 H), 3.92 (s, 4 H), 7.07 (d, J=9.0 Hz, 2 H), 7.43 (d, J=9.0 Hz, 2 H), 7.67 (s, 1 H), 12.40 (brs, 1 H); MS (ES) m/z: 346.8 (MH+); HRMS Calcd. for C17H19N2O4S(MH+): 346.0987. Found: 346.0994. Anal. Calcd. for C17H18N2O4S: C, 58.94; H, 5.24; N, 8.09. Found: C, 58.92; H, 5.11; N, 7.96.

Provenance & Evidence