Chlorosuccinimide → 5-Chloro-2-formylamino-4-(4-formylaminophenylthiomethyl)thiazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-formylamino-4-(4-formylaminophenylthiomethyl)thiazole (2.9 g) in acetic acid (30 ml) was portionwise added N-chlorosuccinimide at 50° C. with stirring. The mixture was heated at 50° C. with stirring. The reaction mixture was concentrated under reduced pressure and the residue was triturated with water. The mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran (1:1), washed with water and dried over magnesium sulfate. The solvent was concentrated under reduced pressure to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 150 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the objective compound were combined and concentrated under reduced pressure to give 5-chloro-2-formylamino-4-(4-formylaminophenylthiomethyl)thiazole (2.0 g, yield: 61.2%). mp: 130°-150° C. (dec.) IR (Nujol): 3350, 3200, 1710, 1690-1640, 1590 cm-1

Provenance & Evidence