Nitrobenzene → 1-(3'-Nitrophenylamino)-5-phenylmercaptoanthraquinone

Participants

Reaction Steps

A mixture of 23.2 parts of 1-amino-5-phenylmercaptoanthraquinone, 14.35 parts of 1-chloro-3-nitrobenzene, 7 parts of sodium carbonate and 140 parts of nitrobenzene is dehydrated in the course of one hour, whilst stirring at the boiling point and whilst passing a stream of nitrogen through the mixture. After adding 0.42 part of copper-I chloride, the mixture is kept at 205°-210° for 18 hours, whilst a moderate stream of nitrogen is passed through. After cooling to 20°, the reaction product is filtered off, washed with nitrobenzene, ethanol and hot water and finally heated to the boil with 5% strength hydrochloric acid, filtered off, washed until acidfree and dried. This gives 25.7 parts (81% of theory) of 1-(3'-nitrophenylamino)-5-phenylmercaptoanthraquinone; melting point 246°. The colorant dyes polyester orange in bulk.

Provenance & Evidence