1,2-Dichlorobenzene → 1-(4-Nitroanilino)-5-(phenylsulfanyl)anthracene-9,10-dione

Participants

Reaction Steps

A mixture of 9.87 parts of 1-bromo-5-phenylmercaptoanthraquinone (melting point 191°-193°), 4.32 parts of 4-nitroaniline, 2.5 parts of sodium carbonate, 58 parts of o-dichlorobenzene, 6 parts of toluene and a solution of 0.4 part of copper-I iodide in 1.5 parts of pyridine is heated to the boil (160°-165°) for 24 hours, whilst stirring. The water which is liberated in the course of the reaction is separated off by means of a water separator. After stirring for 3 hours at 20°, the reaction product is filtered off, washed in portions with a little o-dichlorobenzene, then with methanol and also with water and finally heated to the boil with 5% strength hydrochloric acid. After filtering, washing and drying, 9.03 parts, that is to say 80% of theory, of 1-(4'-nitrophenylamino)-5-phenylmercaptoanthraquinone with a melting point of 242°-244° are obtained. The properties of this compound are completely identical to those of the colorant obtained according to Example 1.

Provenance & Evidence