DE122607C - - Google Patents
Info
- Publication number
- DE122607C DE122607C DENDAT122607D DE122607DA DE122607C DE 122607 C DE122607 C DE 122607C DE NDAT122607 D DENDAT122607 D DE NDAT122607D DE 122607D A DE122607D A DE 122607DA DE 122607 C DE122607 C DE 122607C
- Authority
- DE
- Germany
- Prior art keywords
- phosphorus
- thioacridone
- mesochloracridine
- bromine
- mesobromacridine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- FLCWLOFMVFESNI-UHFFFAOYSA-N 10H-acridine-9-thione Chemical compound C1=CC=C2C(=S)C3=CC=CC=C3NC2=C1 FLCWLOFMVFESNI-UHFFFAOYSA-N 0.000 claims description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N Phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- VIZLMXQJBOYAIH-UHFFFAOYSA-N 1-chloroacridine Chemical compound C1=CC=C2C=C3C(Cl)=CC=CC3=NC2=C1 VIZLMXQJBOYAIH-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N Acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JV! 122607 -KLASSE 12/?. - JV! 122607 - CLASS 12 / ?.
Patentirt im Deutschen Reiche vom 19. Juni 1900 ab.Patented in the German Empire on June 19, 1900.
Aus dem im Patent 120586 beschriebenen Thioakridon läfst sich leicht durch Behandlung mit Phosphorpentachlorid bezw. Brom und rothem Phosphor das sonst schwer zugängliche Mesochlor- bezw. Mesobromakridin darstellen.From that described in patent 120586 Thioacridone can be easily obtained by treatment with phosphorus pentachloride respectively. Bromine and red phosphorus, the otherwise difficult to access mesochlor or. Represent mesobromacridine.
i. Mesochlorakridin.
500 g Thioakridon werden mit 500 g Phosphorpentachlorid und 250 g Phosphoroxychlorid
vermischt im Oelbade unter Rückflufs langsam auf 120 bis 125° erwärmt. Das Ende der
Reaction ist daran zu erkennen, dafs das entstandene Chlorakridin in grüngelben Nadeln
zu sublimiren beginnt. Hierauf wird das Phospboroxychlorid abdestillirt und der Rückstand
nach dem Erkalten mit 10 bis 20 proc. Salzsäure extrahirt, wobei das Mesochlorakridin
in Lösung geht. Aus dem Filtrat wird das Chlorakridin durch Versetzen mit Ammoniak
unter Kühlung ausgefällt. Zur völligen Reinigung wird es in wenig Alkohol gelöst und die
filtrirte Lösung mit Wasser, dem geringe Mengen Ammoniak beigemischt waren, bis zur
bleibenden Trübung versetzt. Es krystallisirt alsdann das reine Mesochlorakridin aus vom
F. P. i22°. In Gegenwart von Salzsäure geht es in der Wärme leicht in Akridon über. Das
Mesochlorakridin ist bereits in der Literatur beschrieben. Graebe und Lagodzinski erhielten
es aus Akridon und Phosphorpentachlorid (Liebig's Ann. Bd. 276, S. 48). Nach vorliegendem Verfahren wird es in reinerer
Form gewonnen, wodurch sich der höhere Schmelzpunkt erklärt; im Uebrigen sind aber
die Producte identisch.i. Mesochloracridine.
500 g of thioacridone are mixed with 500 g of phosphorus pentachloride and 250 g of phosphorus oxychloride and slowly heated to 120 ° to 125 ° in an oil bath under reflux. The end of the reaction can be recognized by the fact that the chloracridine formed begins to sublime in green-yellow needles. The phosphorus oxychloride is then distilled off and, after cooling, the residue contains 10 to 20 percent. Hydrochloric acid extracted, with the mesochloracridine going into solution. The chloracridine is precipitated from the filtrate by adding ammonia with cooling. For complete purification, it is dissolved in a little alcohol, and the filtered solution is mixed with water, to which small amounts of ammonia have been admixed, until it remains turbid. The pure mesochloracridine then crystallizes from the FP 122 °. In the presence of hydrochloric acid, it easily transforms into akridon in the heat. The mesochloracridine has already been described in the literature. Graebe and Lagodzinski obtained it from akridon and phosphorus pentachloride (Liebig's Ann. Vol. 276, p. 48). According to the present process, it is obtained in a purer form, which explains the higher melting point; but otherwise the products are identical.
2. Mesobromakridin.2. Mesobromacridine.
In das gekühlte Gemisch von 200 g Thioakridon und 40 g rothem Phosphor läfst man allmählich 600 g Brom einlaufen. Nach beendigter Reaction wird etwa 20 Minuten auf ioo° erwärmt und hierauf nach dem Erkalten mit 30 bis 40 proc. Schwefelsäure versetzt. Man läfst nun mindestens 1 bis 1Y2 Stunden stehen, filtrirt alsdann und fällt aus dem Filtrat mit Ammoniak das Mesobromakridin. Diesem ist noch ein zweiter basischer Körper vom F. 25 5 ° beigemengt, der sich aber vom Mesobromakridin durch seine Unlöslichkeit in kaltem Aether trennen läfst. Die völlige Reinigung des Mesobromakridins geschieht durch Umkrystallisirung wie beim Mesochlorakridin. Es schmilzt bei 116 bis 1170.600 g of bromine are gradually run into the cooled mixture of 200 g of thioacridone and 40 g of red phosphorus. After the reaction has ended, the mixture is heated to 100 ° for about 20 minutes and then, after cooling, with 30 to 40 percent. Sulfuric acid added. Referring now to läfst least 1 stand up 1Y 2 hours then filtered, and precipitated from the filtrate with ammonia the Mesobromakridin. A second basic body of 25 ° F. is added to this, but it can be separated from the mesobromacridine by its insolubility in cold ether. The complete purification of the mesobromo acridine occurs by recrystallization, as in the case of mesochloro acridine. It melts at 116 to 117 0 .
Die gemäfs vorliegendem Verfahren darstellbaren Prodpcte sollen zur Farbstoffdarstellung Verwendung finden.The products that can be prepared according to the present method are intended for the preparation of dyes Find use.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE122607C true DE122607C (en) |
Family
ID=391518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT122607D Active DE122607C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE122607C (en) |
-
0
- DE DENDAT122607D patent/DE122607C/de active Active
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