Abstract
AbstractA new and general synthesis of 2,l‐benzisothiazolin‐3‐ones (2) is described from the corresponding isatoic anhydride (3) and potassium hydrogen sulfide which gives the thioanthranilic acid (4) which is readily oxadized and ring closed to 2 with hydrogen peroxide. Phosphorus oxy‐chloride converted 3‐hydroxy‐2,1‐benzisothiazole to 3‐chloro‐2,1‐benzisothiazole which gave a number of different 3‐substiluted 2,1‐benzisothiazolesby nucleophilic substitution of the 3‐chloro group. Rleetrophilie substitution of 1‐methyl‐2,1 ‐benzisothiazoIin‐3‐one (2i) proceeded readily to give the corresponding 5‐bromo‐, 5‐nitro‐, and 5‐chlorosulfonyl‐1‐methyl‐2,1‐benzisothiazolin‐3‐one. This appears to be a good synthetic route to such 2,1‐benzisothiazole derivatives.
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