W Nitrochlorobenzene

The reduction of w-nitrochlorobenzene to the corresponding amine by ethanolic stannous chloride follows simple second order kinetics . The reaction is retarded by addition of acid but no effort was made to preserve constant ionic strength. 

An iron condenser should not be used in the steam distillation of the crude w-nitrochlorobenzene, as some reduction takes place and the yield is lowered by 10 to 15 per cent. The product is also deeply colored. 

A meta-nitro group does not produce a similar activating effect. For example, w-nitrochlorobenzene gives no corresponding reaction. 

Desseigne Rabussier (Ref 3) prepd it by heating 2-nitrochlorobenzene, aniline Na carbonate for 9 hts at 193—200°, cooling, and pouting the mixt into w at 40—50°... 

In this connection it is perhaps worthwhile to reconsider the synthesis of benzothiazoline-2-thiones. These substances can, as already mentioned, be made from o-nitrochlorobenzene with sodium hydrogen sulfide and carbon disulfide (method C). Starting from 0- or w-halo anilines, benzothiazoline-2-thiones are also obtainable with carbon disulfide in strong alkali (55). The intermediate in this reaction is an aryne (CXXXIII). 

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