DE376471C - Process for the preparation of 1-chloro-2-acylaminoanthraquinones - Google Patents

Process for the preparation of 1-chloro-2-acylaminoanthraquinones

Info

Publication number
DE376471C
DE376471C DEK74484D DEK0074484D DE376471C DE 376471 C DE376471 C DE 376471C DE K74484 D DEK74484 D DE K74484D DE K0074484 D DEK0074484 D DE K0074484D DE 376471 C DE376471 C DE 376471C
Authority
DE
Germany
Prior art keywords
chloro
acylaminoanthraquinones
preparation
parts
sulfuryl chloride
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.)
Expired
Application number
DEK74484D
Other languages
German (de)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to DEK74484D priority Critical patent/DE376471C/en
Application granted granted Critical
Publication of DE376471C publication Critical patent/DE376471C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
    • C07C233/33—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

Description

Verfahren zur Herstellung von 1-Chlor-2-acylaminoanthrachinonen. Die Darstellung von i-Chlor-2-acetaminoanthrachinoa gelingt nach den Patentschriften 224073 und =9g758. Bei diesen beiden Verfahren wird Eisessig in erheblichen Mengen als Lösungs- bzw. Umlagerungsmittel benötigt. Es wurde nun gefunden, daß i-Chlor-2-acetaminoanthrachinon auch ohne Verwendung des kostspieligen Eisessigs in überraschend glatter Weise durch Behandeln von ß-Acetaminoanthrachinon mit Sulfurylchlorid, zweckmäßig bei Gegenwart von indifferenten Lösungsmitteln, gewonnen werden kann. Beispiel i. 3 Gewizhtsteile ß - Acetaminoanthrachinon werden in 25 Volumenteilen Nitrobenzol heiß gelöst und nach dem. Abkühlen 6 Gewichtsteile Sulfurylchlorid unter fortwährendem Erwärmen am Wasserbade in etwa 3 Portionen zugefügt. Nach etwa einstündigem Erwärmen am Wasserbade, wobei die Reaktionsmasse fast völlig in Lösung geht, wird mit dem mehrfachen Volumen Alkohol versetzt. Es kristallisiert hierauf sofort reines i-Chlor-2-acetaminoantlxrachinon vom Schmelzpunkt 241' aus.Process for the preparation of 1-chloro-2-acylaminoanthraquinones. the Preparation of i-chloro-2-acetaminoanthrachinoa succeeds according to the patents 224073 and = 9g758. Both of these processes use glacial acetic acid in significant quantities needed as a solvent or rearrangement agent. It has now been found that i-chloro-2-acetaminoanthraquinone surprisingly smoothly even without using the expensive glacial acetic acid Treating ß-acetaminoanthraquinone with sulfuryl chloride, expediently in the presence of indifferent solvents, can be obtained. Example i. 3 weight parts ß - Acetaminoanthraquinone are dissolved in 25 parts by volume of nitrobenzene and hot after this. Cooling 6 parts by weight of sulfuryl chloride with continued heating added in about 3 servings at the water bath. After about an hour of warming up at the water bath, whereby the reaction mass goes almost completely into solution, becomes with the multiple volume Alcohol added. Pure i-chloro-2-acetaminoantlxrachinone then immediately crystallizes from the melting point 241 '.

In gleicher Weise wie aus ß-Acetaminoanthrachinon kann man auch aus anderen Acylaminoanthrachinonen die entsprechenden Chlorsubstitutionsprodukte gewinnen. So erhält man aus p Toluolsulfo-ß-aminoanthrachinon, analog obigem Beispiel mehrere Stunden mit Sulfurylchlorid behandelt, glatt das noch unbckannte i-Chlor-2-p-toluolsulfaminoanthrachinon in Form grünlichgelber, bei 204 bis 205' unter Zersetzung schmelzenden Nadeln. Das erhaltene Produkt löst sich in konz. Schwefelsäure mit fuchsinroter Farbe und gibt bei schwachem Erwärmen unter Farbenumschlag nach Orange sofort reines i-Chlor-2-aminoanthrachinon. Beispiel 2. 2 Teile p-Toluolsulfo-ß-aminoanthrachinon werden mit =o Teilen geschmolzenem, pulverisiertem Borax und 15 Teilen Sulfurylchlorid während fünf Stunden auf eine Temperatur von etwa ioo bis iio ° im geschlossenen Rohr erhitzt. Das erhaltene Reaktionsprodukt wird mit heißer, wäßriger Natronlauge behandelt, wobei die Natriumverbindung des gebildeten i-Chlor-2-p-toluolsulfaminoanthrachinons als roter kristallinischer Niederschlag zurückbleibt, während unverändertes Ausgangsmaterial in Lösung geht. Durch Zerlegen des roten Natriumsalzes (C6H4(CO2)2C6H2 - Cl - N - Na . SO2 - C77) mit Salzsäure und wiederholte Kristallisation des erhaltenen Produktes aus Eisessig erhält man reines i-Chlor-2-p-toluolsulfaminoa.nthrachinon.In the same way as from ß-acetaminoanthraquinone, the corresponding chlorine substitution products can also be obtained from other acylaminoanthraquinones. Thus, from p toluenesulfo-ß-aminoanthraquinone, treated with sulfuryl chloride for several hours analogously to the above example, the as yet unknown i-chloro-2-p-toluenesulfaminoanthraquinone is obtained smoothly in the form of greenish-yellow needles that melt at 204 to 205 'with decomposition. The product obtained dissolves in conc. Sulfuric acid with a fuchsin red color and, when heated slightly, immediately gives pure i-chloro-2-aminoanthraquinone with a color change to orange. Example 2. 2 parts of p-toluenesulfo-β-aminoanthraquinone are heated with = 0 parts of molten, powdered borax and 15 parts of sulfuryl chloride for five hours to a temperature of about 100 to 100 ° in a closed tube. The reaction product obtained is treated with hot, aqueous sodium hydroxide solution, the sodium compound of the i-chloro-2-p-toluenesulfaminoanthraquinone formed remaining as a red crystalline precipitate, while unchanged starting material dissolves. By decomposing the red sodium salt (C6H4 (CO2) 2C6H2 - Cl - N - Na. SO2 - C77) with hydrochloric acid and repeated crystallization of the product obtained from glacial acetic acid, pure i-chloro-2-p-toluenesulfaminoa.nthraquinone is obtained.

Claims (1)

PATENT-ANSPRUcH: Verfahren zur Herstellung von i-Chlor-2-acylaminoanthrachinonen, dadurch gekennzeichnet, daß man ß-Acylaminoanthrachinone mit Sulfurylchlorid zweckmäßig bei Gegenwart indifferenter Lösungsmittel behandelt.PATENT CLAIM: Process for the production of i-chloro-2-acylaminoanthraquinones, characterized in that ß-acylaminoanthraquinones with sulfuryl chloride are expedient treated in the presence of inert solvents.
DEK74484D 1920-09-23 1920-09-23 Process for the preparation of 1-chloro-2-acylaminoanthraquinones Expired DE376471C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEK74484D DE376471C (en) 1920-09-23 1920-09-23 Process for the preparation of 1-chloro-2-acylaminoanthraquinones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEK74484D DE376471C (en) 1920-09-23 1920-09-23 Process for the preparation of 1-chloro-2-acylaminoanthraquinones

Publications (1)

Publication Number Publication Date
DE376471C true DE376471C (en) 1923-05-29

Family

ID=7232454

Family Applications (1)

Application Number Title Priority Date Filing Date
DEK74484D Expired DE376471C (en) 1920-09-23 1920-09-23 Process for the preparation of 1-chloro-2-acylaminoanthraquinones

Country Status (1)

Country Link
DE (1) DE376471C (en)

Similar Documents

Publication Publication Date Title
DE376471C (en) Process for the preparation of 1-chloro-2-acylaminoanthraquinones
US2715644A (en) Purification of sodium gentisate
DE488606C (en) Process for the preparation of benzanthrones
DE377587C (en) Process for the preparation of mono- and dichloro-1-ketotetrahydronaphthalene
DE470503C (en) Process for the preparation of anthraquinone derivatives
DE608434C (en) Process for the preparation of condensation products from 2,3-oxynaphthoic acid and anthranilic acid amide or its substitution products
DE750398C (en) Process for the preparation of 3- and 4-oxypyridine-4- and -3-carboxylic acids
DE69035C (en) Process for the preparation of p-ethoxyacetylamidoquinoline. (4th
DE259365C (en)
DE503031C (en) Process for the preparation of the N-oxyethyl derivatives of core substitution products of -amino-1-oxybenzene
DE201325C (en)
DE929729C (en) Process for purifying dehydrocholic acid
DE499824C (en) Process for the preparation of 4-aminodiphenylamine derivatives
DE701561C (en) orbic acid
DE543112C (en) Process for the preparation of 2-phenyl-4-oxy-6-amino-1, 3, 5-triazines
DE968754C (en) Process for the production of pellets of aromatic sulfonamides
DE630021C (en) Process for the preparation of 4,5-alkyl-substituted 2-aminodiaryl ketones
DE574839C (en) Process for the preparation of clusters of monohalo-N-alkyl-2-pyridones
DE701464C (en) Process for the preparation of o-halogenanthraquinone-ª -carboxylic acids
DE291614C (en)
DE492248C (en) Process for the preparation of halobenzanthrones
DE396509C (en) Process for the preparation of nitrogen-containing anthraquinone derivatives
DE505321C (en) Process for the production of naphthostyrils monochlorinated in the core
DE496393C (en) Process for the preparation of anthraquinone and its offshoots
DE234631C (en)