H3c

H2N-SO2

H CH3

H CH3

H2N-SO2

Metolazone acts on the distal tubules, thus increasing excretion of water and sodium, potassium, and chloride ions. It is used for treating edema caused by cardiac insufficiency and adrenal irregularities, including nephrotic syndrome. Synonyms of this drug are diulo, matenix, and zaroxolyn.

Chlorothalidone: Chlorothalidone, 2-chloro-5-(1-hydroxy-3-oxo-1-isoindolinyl)benzol-sulfamide (21.3.26), is synthesized by two proposed methods from 2'-carboxy-4-chloroben-zophenone (21.3.21), which is easily synthesized by acylating chlorobenzol with phthalic anhydride in the presence of aluminum chloride. The resulting benzophenone (21.3.21)

Cl cl undergoes nitration by nitric acid, which gives 2'-carboxy-3-nitro-4-chlorobenzophenone (21.3.22). The nitro group in the resulting compound is reduced by tin dichloride to 2'-carboxy-3-amino-4-chlorobenzophenone (21.3.23). Next, subsequent diazotation and reaction with sulfur dioxide in the presence of copper dichloride gives the corresponding sul-fonylchloride (21.3.24). Upon reaction with thionyl chloride, this compound undergoes cyclization into phtahlide (21.3.25), which when reacted with aqueous ammonia rearranges into a derivative of isoindoline with simultaneous substitution of the chloride atom in the sul-fogroup with an amino group, which results in chlorothalidone (21.3.26) [48,49].

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