Wi-Toluidine

Many diazonium solutions have been reported to react explosively with solutions of metallic polysulfides even at low temperatures.12 A violent reaction with xanthates is mentioned only in one report.3 Neither the authors nor the checkers observed any unusual reactivity during this preparation or with the procedure given for dithiosalicylic acid.4 On a large scale (100 moles of wi-toluidine) flashes of light have been occasionally observed (private communication, L. J. Roll). 

One hundred and six grams (i mole) of benzaldehyde (Note i) and 107 g. (i mole) of w-toluidine are mixed in a suitable flask the temperature rises to about 60 (Notes 2 and 3). The mixture is cooled below 35° in cold water, 200 cc. of ether is added, and the solution is placed in the steel reaction vessel of a high-pressure hydrogenation apparatus. Eight to ten grams of Raney nickel catalyst (p. 15) is added, the bomb is closed, and hydrogen is admitted up to 1000 lb. pressure (Note 4). The bomb is shaken continuously at room temperature for fifteen minutes (Note 5). The contents are removed, and the bomb is washed out with two 200-cc. portions of ether. After the catalyst has been separated by filtration (Note 6), the ether is removed by distillation and the product is distilled from a modified Claisen flask (Note 7). After a small fore-run the iV-benzyl-wi-toluidine boils at i53-i57°/4 3iS 3i7°/76o mm. The yield is... 

The following compounds are reported to have been deaminated by decomposing their stabilized diazonijim salts aniline 8 o-, m-, and p-toluidine 6 o-, m-, and p-anisidine 6 o-, m-, and p-nitroaniline 8 2-methoxy-4-nitro-5-aminotoluene 101 m-phenylenediamine 8 wi-tolyl-enediamine 8 p-aminophenol 8 benzidine 8 a- and /3-naphthylamine. . ) ... 

Also highly nitrated compounds can be detected and identified by means of donors, such as hydrocarbons. Their identification was suggested by the method of thin-layer chromatography [103]. A method of rapid detection, of explosives such as TNT, TNB, Picryl chloride, wi-DNB, Tetryl in the form of charge-transfer complexes with aromatic amines, such as aniline, dimethylaniline, toluidines, anisidines, naphthylamines, benzidine etc. was developed by Dwivedy et al. [104]. The authors used for identification thin-layer chromatography establishing Rf values for model complexes. 

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