GB1246254A - Diazonium compounds and their use in diazotype processes - Google Patents

Abstract

1,246,254. Diazonium compounds. OCE VAN DER GRINTEN N.V. 20 Jan., 1970 [27 Jan., 1969], No. 2754/70. Heading C2C. [Also in Division G2] The invention comprises compounds of the formula wherein X represents an anion, R 1 and R 2 represent alkyl, aralkyl, cycloalkyl or other hydrocarbon residues or together with the N- atom constitute a heterocyclic ring which may contain a further hetero atom and may contain substituent groups; R 3 represents H, CH 3 , halogen, alkoxy, alkylthio, arylthio, aralkylthio or a group where R 4 represents alkyl, aralkyl or cycloalkyl and -COR 5 represents a carboxylic or carbonic acyl group in which R 5 is H or an organic radical. They may be obtained by diazotization of the corresponding amines. Examples are given for the production of the compounds. They are useful in diazotype processes. 4 - Dimethylamino - 3 - phenyl - 1 - nitrobenzene is obtained by reducing 2-nitrodiphenyl to 2-aminodiphenyl, reacting this compound with tosyl chloride to give 2-tosylamino-diphenyl, nitrating this compound to give 4-tosylamino-3- phenyl - 1 - nitrobenzene, hydrolysing this compound to give 4-amino-3-phenyl-1-nitrobenzene, diazotizing this compound and reacting with cuprous chloride in HC1 to give 4-chloro-3- phenyl- 1-nitrobenzene, reacting this compound with (CH 3 ) 2 NH to give 4-dimethylamino-3- phenyl- 1 -nitrobenzene. 4 - N - methyl - N - cyclohexylamino - 5 - phenyl - 2 - chloro 1 - nitrobenzene is obtained by diazotizing 4 - chloro - 2 - nitro - aniline and adding to the diazonium solution (CH 3 ) 2 NH to obtain 4 - chloro - 2 - nitro - 1 - dimethylamino-azo-benzene, reacting this compound with p-toluene sulphonic acid to give 5-chloro-2- phenyl- 1 -nitrobenzene which is catalytically reduced to 5-chloro-2-phenyl-aniline, reacting this compound with tosyl chloride to give tosyl - 5 - chloro - 2 - phenyl - aniline, nitrating this compound to give 4-tosylamino-5-phenyl- 2-chloro-1-nitrobenzene, hydrolysing this compound with conc. H 2 SO 4 to give 4,-amino-5- phenyl - 2 - chloro - 1 - nitrobenzene, cyclohexylating this compound to give 4:-cyclohexylamino 5 - phenyl - 2 - chloro - 1 - nitrobenzene which is methylated to give the required product. 4 - N - methyl - N - cyclohexylamino - 5 - phenyl - 2 - N - methyl - N - ethoxycarbonylamino-1-nitrobenzene is obtained by reacting 4 - N - methyl - N - cyclohexylamino - 5 - phenyl- 2 - chloro - 1 nitrobenzene with CH 3 NH 2 to give 4 - N - methyl - N - cyclohexylamino - 5 - phenyl - 2 - methylamino - 1 - nitrobenzene, reacting this compound with ethyl chloroformate to give the required product.