DE224982C - Process for the preparation of arylsulfaminoanthions - Google Patents

Description

IMPERIAL

PATENT OFFICE.

IDENTIFICATION

- Jig 224982 CLASS 12 g. GROUP

Dr. FRITZ ULLMANN in BERLIN.

Process for the preparation of arylsulfaminoanthraquinones,

Patented in the German Empire on July 20, 1909 .

Halogenanthraquinones with aryl sulfamides in an extraordinarily smooth manner with formation

react:

E.g.

-I- NH ₂ -SO ₂ -R =

+ HCl.

40

45

The reaction is conveniently carried out using a catalyst and in the presence made of hydrochloric acid binding agents.

The new compounds are said to be used as starting materials for the manufacture of dyes to serve.

Example 1.

10 parts of 1-chloranthraquinone, 10 parts of p-tol'uenesulfamide, 8 parts of potassium carbonate, ι part of copper acetate and 100 parts of nitrobenzene are refluxed to the boil. The solution soon turns red, and the reaction is complete after two to three hours. After the nitrobenzene has been driven off, what remains is almost completely pure 1 - ρ - toluenesulfamino- 'anthraquinone. By recrystallising from glacial acetic acid to get it in the form of beautiful yellow needles melting at 225 ⁰ and are insoluble in alcohol and ether.

Example 2.

The ι - chloranthraquinone of Example 1 can be replaced by the 2 - iodoanthraquinone, which one according to the method followed by Scholl in the preparation of 2-methyl-i-iodanthraquinone (Ber. 40 [1907], p. 1696) from 2 - Aminoanthraquinone can be obtained. The 2-Jodanthrachinon forms almost colorless, heavy in ether and ligroin, readily soluble in nitrobenzene at 170 ⁰ needles melting. If 2 parts of 2-iodoanthraquinone, 2 parts of p-toluenesulfamide, 1.6 parts of potassium carbonate, 0.2 part of copper and 0.2 parts of copper acetate in 20 parts of nitrobenzene are slowly heated to 180 °, the temperature then increases to 200 to within 4 hours 210 ⁰ (oil bath temperature), the toluenesulf ^ -aminoanthraquinone is obtained after the nitrobenzene has been driven off from the acidified reaction mass. It is rather difficult to dissolve in the usual agents and crystallizes from acetic anhydride in yellowish needles. These dissolve in dilute caustic soda with an orange color. Brief heating with concentrated sulfuric acid produces 2-aminoanthraquinone.

Example 3.

12 parts of 1 - chloranthraquinone, 15 parts of anthraquinone - 2 - sulfamide, 100 parts of nitrobenzene,,

7 parts of potassium carbonate and ι part of copper acetate are ^{heated to boiling for 1} J ₂ hours, the mass turning red. The residue that remains after the nitrobenzene has been drained off is first boiled with lye and then with benzene, leaving the i, 2'-anthraquinonylsulfaminoanthraquinone as a beautiful yellow colored crystal powder, which is almost insoluble in the common solvents and of concentrated sulfuric acid with an orange-red color is recorded.

Example 4.

20 parts of 1 · 5-dichloroanthraquinone, 40 parts Benzolsulf amide, 20 parts of potassium carbonate, 1 part of copper acetate and 200 parts of nitrobenzene are heated for 5 hours at 200 ° to 210 ^0th When the red melt is worked up, the 1 · 5-dibenzenesulfodiaminoanthraquinone remains as a yellow crystal powder. It is insoluble in alcohol, ether and benzene and is easily absorbed by the boiling nitrobenzene.

Claims (1)

Patent claim: Process for the preparation of arylsulfaminoanthraquinones, consisting in the fact that one halanthraquinones and their derivatives on aryl sulfamides, expediently Presence of catalysts and hydrochloric acid binding agents.