Dimethylformamide → 5-(Quinoline-2-sulfonyl)-thiazolidine-2,4-dione

Participants

Reaction Steps

30% Aqueous hydrogen peroxide (10.7 mL, 104 mmol) was added dropwise to a stirred solution of 2-quinolinethiol [(II), 8.0 g, 49.6 mmol] in 2.5% aqueous NaOH (229 mL) and ethanol (229 mL). After 1 h the reaction mixture was concentrated to provide a white solid (8.34 g) which contained mainly sodium-2-naphthalenesulfinate (formula IV). A 7.0 g portion of this compound (<32.5 mmol) was added to a solution of 5-bromo-thiazolidine-2,4-dione (6.38 g, 32.5 mmol) in dry DMF (53 mL) and the resultant solution was stirred at room temperature for 4 h. The DMF was removed in vacuo and water (400 mL) was added to the residue. The water phase was extracted with ethyl acetate (2×400 mL) and the combined ethyl acetate phase was dried (brine) and concentrated. The crude product was flash chromatographed (gradient: 98:2 to 97:3 CH2Cl2 : isopropanol) to provide the title compound as a yellow solid (1.1 g, 9%): mp 168°-169° C.; NMR (DMSO, d 6): δ12.9 (broad s, 1H, NH), 8.85 (d, J=8.8 Hz, 1H, ArH), 8.24 (d, J=8.1 Hz, 1H, ARH), 8.16 (d, J=8.7 Hz, 2H, ArH), 8.02 (dd, J=6.9, 8.3 Hz, 1H, ArH), 7.89 (dd, J=6.9, 8.1 Hz, 1H, ArH), 6.95 (s, 1H, CH); MS(EI): 308 (MI, 10%), 265 (8%), 145 (18%), 129 (100%), 128 (75%); Anal. (C12H8N2O4S2): C, H, N.

Provenance & Evidence