Studies on Isothiazoles. II. Nitration of 3-Phenylisothiazoles

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Abstract
Nitration of 4-substituted-3-phenyliosthiazoles (I, II, III, and IV) with fuming nitric acid and sulfuric acid yielded exclusively the corresponding 3-m-nitrophenyl derivatives (VI, VII, VIII and IX), while nitration of 3-phenylisothiazole (V) gave 3-p-nitrophenylisothiazole (Xa) and 3-m-nitrophenylisothiazole (Xb). Reduction of 5-methyl-3-m-nitrophenylisothiazole-4-carboxylic acid (IX) afforded the corresponding amino derivative (VII), which was diazotized and subjected to the Sandmeyer Reaction to give the corrsponding 3-m-chlorophenyl (XIV) and 3-m-bromophenyl (XV) derivatives. Preparation of the 3-m-methoxyphenyl derivative (XVII) was also described.

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