DE518406C - Process for the preparation of 1-aroylamino-4-haloanthraquinones - Google Patents

Description

Process for the preparation of 1-aroylamino-4-haloanthraquinones It has been found that the preparation of i-aroylamino-4-halogenanthraquinones by the action of halogen or halogen-releasing agents, such as. B. Sulfuryl chloride, based on 1-Araylaminaanthraquinones in inert solvents in The presence or absence of catalysts such as iodine or ferric chloride is extraordinary runs easily. Dihalogen products which are formed simultaneously in many cases during the reaction arise in such a small amount that they are produced when the reaction mixture is worked up Remain dissolved in the applied inert solvent and thus the monohalogen derivatives can be obtained directly pure and free from dihalogen derivatives. This is remarkable since from i-acetylaminoanthraquinone by the same process almost only dihalogen derivatives can be obtained.

Example i 509 i-Benzoylaminoanthraquinone are suspended in zoo g of nitrobenzene. 126g of sulfuryl chloride were added and the mixture was stirred at 60 ° for 15 hours. : After cooling, the precipitated i-benzoylamino-4-chloroanthraquinone is sucked off and washed with alcohol.

EXAMPLES 509 i-Benzoylaminoanthraquinone are stirred in zoo cc of nitrobenzene, and elemental chlorine is passed into this suspension at 60 °. Work-up as under i.

Example 3 34 g of i-aminoanthraquinone are dissolved in 72 cc of nitrobenzene suspended, added 23.5 g of benzoyl chloride and heated to 1200 for one hour. The mixture is then allowed to cool to 60 °, 849 sulfuryl chloride is added and the mixture is held for 15 hours long at the specified temperature. Work up as under i.

Other aroylamino-4-halogenanthraquinones can also be used in an analogous manner represent if, in place of the benzoyl chloride, other aroyl halides, such as. B., toluyl chloride, is used.

Example 4 68; 2 g of i-aminoanthraquinone are dissolved in 400 g of tetrachloroethane stirred and allowed to drop in 48 g of benzoyl chloride at i20 °. After completion the benzoylation is cooled to 60 °, and 250 g of sulfuryl chloride are added. The temperature is held until no more unchanged benzoylaminoanthraquinone is demonstrable. Work up as under i.

Example 50 g of i-benzoylaminoanthraquinone are converted into zoo cc of nitrobenzene suspended, 0.5 g of iodine and 126 g of sulfuryl chloride were added. To to the At the end of the reaction, the temperature is kept at 40 °. Work-up as below i.

Example 6 20 g of i-benzoylaminoanthraquinone are dissolved in 40 cc of nitrobenzene stirred, 0.3 g of ferric chloride and 29 g of bromine were added. The temperature will be on 40 ° held. If unchanged starting material is still available, after Another 18 g of bromine were added about 12 hours and continued until the reaction had ended held at 400. After it has cooled down, it is sucked off, washed with alcohol and, if necessary, recrystallized from nitrobenzene or another organic solvent.

The yield of pure i-aroylamino-4-halogenanthraquinones in the above examples varies between about 63 to 75 % of theory. The effective yield is higher, but in most cases it would not be worthwhile to work up the amounts remaining in the residual liquors because of the separation of mono- and dihalogen products that would then become necessary.

Claims (1)

PATENT CLAIM: Process for the preparation of i-aroylamino-4-halogenanthraquinones, characterized in that i-aroylaminoanthraquinones are treated in inert solvents with or without the addition of catalysts with halogen or halogen-releasing agents.