Ethoxzolamide → 6-Hydroxy-1,3-benzothiazole-2-sulfonamide

Participants

Reaction Steps

To a 1 L round bottomed flask equipped with a magnetic stir bar, rubber septum, and argon inlet containing DCM (500 mL) was placed 6-ethoxybenzo[d]thiazole-2-sulfonamide (25 g, 108.7 mmol). To this solution at 0° C. (ice bath) was added AlCl3 (50 g, 376 mmol) portion-wise and the reaction was allowed to stir at rt for 24 h. Solvent was removed in vacuo and the residue was cautiously quenched into 3 M HCl (600 mL). The mixture was filtered and the solid was washed with cooled 3 M HCl (2×50 mL). The product was dried under high vacuum for 48 h to afford compound 1 as a yellow solid (24 g).

Provenance & Evidence