Lead diacetate trihydrate → N-(4-nitrobenzylmercapto)succinimide

Lead (II) acetate trihydrate (0.759 g, 2.0 mmol) and 4-nitrobenzyl mercaptan (0.745 g, 4.4 mmol) were stirred together in methanol (24 cm3) solution at room temperature. After 1 h, the products were filtered and the residue was washed with a small volume of cold methanol. The residue was dried in vacuo over calcium chloride and then suspended in dry acetonitrile (20 cm3). Following the evaporation of the solvent under reduced pressure, the residue was suspended in dry benzene (20 cm3) and the solvent was again evaporated under reduced pressure. Finally, the residue was re-suspended in dry benzene (64 cm3) and N-bromosuccinimide (0.783 g, 4.4 mmol) was added in three portions over a period of 45 min to the stirred suspension at room temperature. The reactants were then heated at 50° C., under an atmosphere of argon, for 14 h. The cooled products were filtered and the filtrate was evaporated under reduced pressure to give a solid. The latter material was crystallized from ethyl acetate--hexane to give N-(4-nitrobenzylmercapto)succinimide 18 (0.76 g, 65%) (Found: C, 49.85; H, 3.8; N, 10.4. C11H10N2O4S requires: C, 49.6; H, 3.8; N, 10.5%), m.p. 146°-148° C.; δH [CDCl3 ] 2.73 (4 H, s), 4.18 (2 H, s), 7.50 (2 H, m), 8.17 (2 H, m); δC [CDCl3 ] 28.4, 40.5, 123.8, 130.3, 141.9, 147.5, 176.2.