r 329 ] 



XV. 



OX THE CONDENSATIOX OF XITEOSOPHESTTLUEETHAXE IVITH 

 TOLUTLENEDIAMIXE HYDEOCHLOEIDE. 



By HUGH EYAX, D.Sc, 



AND 



MAEGAEET EGAX, D. es Sc, 

 XJniversity College, Dublin. 



[Eeaii FEBKriiiy 25. Published September 15, 1924.] 



Br the action of nitrous fumes on a solution of phenylurethane in glacial 

 acetic acid E. Willstaetter (Ber. Dtseh. Chem. Ges., xlii, 1909, p. 4876) 

 obtained a veiy unstable pheuylnitrosourethane CgHg . N(XO) . COOC'oHg. 

 An isoiieride of this, ^j-nitrosophenyluretliane, was obtained by T. J. Nolan 

 (private communication from Xobel's Explosives Company) by the action of 

 sodium nitrite on a cold solution of phenylurethane in concentrated sulphuric 

 acid. He also observed that the nitrosourethane gives red colourations with 

 alcoholic solutions of the hydrochlorides of certain amines. 



Since it seemed likely that the coloured products formed by the action of 

 nitrosophenylurethane on aromatic metadiamines were substances of the 

 nature of the indamine or the eurhodiue dyestuffs, the behaviour of 

 nitrosophenylurethane towards m-toluylenediamine was examined. 



O. N. Witt (Ber. Dtsch. Chem. Ges., xii, 1879, p. 931) has shown that a 

 warm, dilute aqueous solution of the hydrochloride of j9-nitrosodimethyl- 

 aniline reacts with 7?i-toluyienediamine to form blue-black crystals of an 

 indamine, Tolylene Blue : — 



aH(CH3)2N 



CH, 



CH, 



NH 



NH£ CIH(CH3)2N\^ HgN 



Tolylene Blce. 

 Witt also showed that when an aqueous solution of Tolylene Blue is 



