DIAZONIUM SALTS

1,237,531. Diazonium salts. ILFORD Ltd. 29 April, 1968 [1 May, 1967], No. 19993/67. Heading C2C. [Also in Division G2] The invention comprises diazonium compounds of the general formula wherein R is phenyl or p-chloro-phenyl; Y is hydrogen, (C 1-6 ) alkyl or alkoxy and, X is an anion such as a chloride or sulphate ion, or a zinc chloride double salt, a cadmium chloride double salt or a borohalide, but excluding a said compound when Y is hydrogen and R is unsubstituted phenyl. In Example I 3-(41-chlorophenoxy), 4-pyrrolidino benzene diazonium sulphate is prepared-the intermediate stages being as follows: (i) p-chlorophenol and 3,4- dichloronitrobenzene are reacted to produce 4-nitro-2,41-dichloro diphenylether, (ii) the nitro compound is reduced to give 4-amino-2,41-dichloro diphenylether, (iii) the amine is acetylated to give 4-acetylamino-2,41-dichloro diphenylether, (iv) the amide is nitrated to produce 4-acetylamino - 2,41- dichloro - 5 - nitro diphenylether, (v) the nitro compound is deacetylated to form 4-amino-2,41-dichloro-5-nitro diphenylether, (vi) the nitroamine is diazotized and reduced to give 2,41-dichloro-5-nitro diphenylether, (vii) the foregoing nitro compound is treated with pyrrolidine to produce 41-chloro-5-nitro, 2-pyrrolidine diphenylether, and (viii) the nitro derivative is reduced and diazotized to give the 3-(41- chlorophenoxy), 4-pyrrolidino benzene diazonium compound which is converted to a sulphate derivative. In Example II 2-methyl, 5-(41-chlorophenoxy), 4-pyrrolidino benzene diazonium zinc chloride is prepared the intermediate stages being as follows: (i) p-chlorophenol and 4-chloro-3-nitrotoluene are reacted to produce 41-chloro, 4-methyl, 2-nitro diphenylether, (ii) the nitro compound is reduced to form 2-amino, 41-chloro, 4-methyl diphenylether, (iii) the amino compound is acetylated to give 2- acetylamino, 41-chloro, 4-methyl diphenylether, (iv) the amide is nitrated to produce 2-acetylammo, 41-chloro, 4-methyl, 5-nitro diphenylether, (v) the nitro amide is deacetylated to form 2- amino, 41-chloro, 4-methyl, 5-nitro diphenylether, (vi) the nitro amine is diazotized, reduced and chlorinated to give 2,41-dichloro, 4-methyl, 5- nitro diphenylether, (vii) the dichloro compound is reacted with pyrrolidine to form 41-chloro, 4- methyl, 5-nitro, 2-pyrrolidino, diphenylether, and (viii) the nitro derivative is reduced and diazotized to give the 2-methyl, 5-(41-chlorophenoxy), 4-pyrrolidine benzene diazonium compound, which is treat