Chloro subs anilines

The selective reduction of nitroarenes containing benzyl-protected phenolic groups without concomitant hydrogenolysis has also been achieved using hydrazine hydrate and Raney nickel. This procedure avoids strongly acidic conditions. The reaction is selective and a variety of (V-benzyl- and chloro-sub-stituted nitroarenes are reduced to the corresponding anilines without dehalogenation or debenzylation. 

B) Preparation of 4-Amino-2-Chloro-5-(Methylsulfamyl)Benzenesulfonamide The 5-sub-stituted-2,4-dlsulfamyl anilines may be prepared by procedures described in the literature, for example, the general procedures in Monatsch. Chem. vol. 48, p 87 (1927), which involves the treatment of a m-substituted aniline with from 10 to 20 parts by weight of chlorosulfonic acid followed by the gradual addition of from about 90 to 170 parts by weight of sodium chloride. The resultant mixture is heated at approximately 150°C for about 2 hours after which the reaction mixture is poured into water and the resultant 5-substituted aniline-2,4-disulfonyl chloride is filtered and is then treated with concentrated ammonium hydroxide or suitable amine by standard procedures to obtain the corresponding disulfonamide. 

The antibacterial agent sulfamethoxazole produced chlorinated and nonchlorinated DBFs when reacted with chlorine [91]. A ring-chlorinated product was formed via halogenation of the aniline moiety at sub-stoichiometiic concentrations of chlorine. 3-Amino-5-methylisoxazole, sulfate, and A-chloro-p-benzoquinone imine were formed via rupture of the sulfamethoxazole sulfonamide moiety at stoichiometric excess of chlorine. 

Finally, a few miscellaneous compounds which were identified in the Delaware River and which have not been previously reported as water contaminants will be discussed Chloro (trifluoromethyl) aniline and chloro (trifluoromethyl) nitrobenzene (no. 55 and 56) were identified in the water, they had maximum concentrations at river mile 78. Both compounds represent common sub-structures in various pesticide and dye molecules, and several of the companies located along the river have patents using these compounds (30-32j. It is possible that these compounds are actually present in the river water as such, but it is also possible that they are formed in the GC injection port by pyrolytic degradation of larger pesticide or dye molecules (see above). All three binaphthyl-sulfone isomers (no. 92) were identified in the river water near Philadelphia. Product literature for one of the companies in the area indicates production of condensed sulfonated polymers derived from naphthalene sulfonic acid and maleic anhydride. It seems likely that the binaphthylsulfones are formed as by-products during preparation of this commercial product. 

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