DE220314C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

PATENT LETTERING

- M 220314 CLASS 12y ?. GROUP 10.

FARBENFABRIKEN vorm. FRIEDR. BAYER & CO. in ELBERFELD.

Process for the preparation of anthrapyrimidines and anthrapyrimidones.

Patented in the German Empire on March 24, 1908.

If acid amides are allowed to act on a- aminoanthraquinones and its derivatives, new anthraquinone derivatives are obtained,

C OO \

/ ■, ■■ ···,

NiH ₉ I \

which have the character of pyrimidines or pyrimidones. The reaction takes place
most likely in the following way: 40

I. a)

CiO

C O

- 2 H, O

NH ₂
Aminoanthrapyrimidine.

NH,

₂₀ When a second molecule of the acid amide acts, further ring closure takes place according to the following scheme:

CH CH

/ V 60

NN ^:

- 2 Η. Ο = ■■

IC

N "'N

■ -. ·

Anthradipyrimidine.

Claims (1)

II. When using the amides of carbonic acid, the reaction proceeds as follows: C 0 + H ₂ O + NH ₃ Anthrapyrimidone. The new bodies are supposed to be used for the representation of dyes as well as medicinal products Find. Example 1. 10 kg ι · 4-diaminoanthraquinone are with 50 kg of formamide heated to 180 ° in an oil bath until the melt assumed a yellow color Has. The reaction product which separates out on cooling is filtered off with suction and recrystallized from nitrobenzene. It educates Pale colored needles, the solution of which in pyridine is colorless, in concentrated sulfuric acid is yellow. It is probably the dipyrimidine formulated in equation I. b) above. Example 2. 10 kg ι · 4-diaminoanthraquinone are boiled with 20 kg of formamide and 40 kg of phenol I ¹ J for ₂ hours, the still warm melt is diluted with the same volume of alcohol and separates on cooling a dark-colored crystal mass, which turns yellow-brown after dissolving with pyridine Prisms', the solution of which in pyridine is yellow with strong green fluorescence, in concentrated sulfuric acid orange-red, and if formaldehyde is added, it is carmine-red. By further heating with formamide, the body changes to that described in Example 1 and evidently represents that 4-amino-i-anthrapyrimidine.,! ^ ;;
Example 3. 10 kg of α-aminoanthraquinone are with 10 kg of urea and 30 kg of phenol boiled for 4 hours. The reaction product (1-anthrapyrimidone) separates after the addition of alcohol when it cools and becomes through Obtained pure crystallization from nitrobenzene. It forms yellow prisms, the solution of which is in Pyridine yellow, in concentrated sulfuric acid orange-yellow with weak fluorescence, in aqueous alkali is orange. The analysis provides numbers that suggest that condensation of the amine with urinary substance has taken place with the escape of one molecule each of water and ammonia: Calculated for C ₁₅ H ₈ O ₂ N ₂ : Found: C = 72.54 percent, 72.59 percent, H = 3.25. - 3.98 N = 1X32 - 11.88 -. Obtained from i-amino-4-p-tolylaminoanthraquinone one in an analogous way bronzing prisms of the 4 - ρ - tolylamino -1 - anthrapyrimidone, its solution in pyridine is red-violet, in concentrated sulfuric acid it is blue. His Sulphonic acid gives wool a vivid purple color. Example 4. 10 kg ι - methylamino - 4 - β - anthraquinonylaminoanthraquinone (obtainable by condensation of i-methylamino-4-aminoanthraquinone with ß-chloranthraquinone according to the method of patents 162824 and 174699 of Class 12 q, dark blue powder, solution in pyridine blue, in concentrated sulfuric acid blue) are cooked with 20 kg of urea, 10 kg of zinc chloride and 80 kg of phenol until the beginning blue melt has turned purple-red. It is poured into excess dilute sodium hydroxide solution, filters the precipitated dye (4-ß-anthraquinonylamino -1 - N - methylanthrapyrimidone) and washes it with hot water and dilute hydrochloric acid. Its solution in concentrated sulfuric acid is dirty blue, first turns green when diluted with water. When precipitated, it forms purple Flakes, which dissolve in alkaline hydrosulfite to form an orange-brown vat, with real red-violet dyeings are obtained on cotton. - Godfather ν τ-A ns pe υ cii: Process for the preparation of anthrapyrimidines and anthrapyrimidones therein consisting that one on a-aminoanthraquinone or its derivatives amides organic Acids or amides of carbonic acid (with the exception of urethanes) can act.