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DE858555C - Process for the preparation of 1-aminonaphthalene-5-sulfonic acid amides - Google Patents

Process for the preparation of 1-aminonaphthalene-5-sulfonic acid amides

Info

Publication number
DE858555C
DE858555C DEB6947D DEB0006947D DE858555C DE 858555 C DE858555 C DE 858555C DE B6947 D DEB6947 D DE B6947D DE B0006947 D DEB0006947 D DE B0006947D DE 858555 C DE858555 C DE 858555C
Authority
DE
Germany
Prior art keywords
sulfonic acid
aminonaphthalene
preparation
acid amides
parts
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
DEB6947D
Other languages
German (de)
Inventor
Helmut Dr Pfitzner
Alfred Dr Simon
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DEB6947D priority Critical patent/DE858555C/en
Application granted granted Critical
Publication of DE858555C publication Critical patent/DE858555C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/47—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
    • 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
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von 1-Aminonaphthalin-5-sulfonsäureamiden Es wurde gefunden, daß man in einfacher Weise i-Aminonaphthalin-5-sulfonsäureamide erhält, wenn man i-Acylaminonaphthaline bei gewöhnlicher oder mäßig erhöhter Temperatur mit überschüssiger Halogensulfonsäure behandelt, die so erhaltenen i-Acylaminonaphthalin-5-sulfonsäurehalogenide mit Ammoniak, primären oder sekundären Aminen oder deren Salzen mit schwachen Säuren, z. B. ihren Carbonaten oder Acetaten, umsetzt und schließlich die Acylgruppe in an sich bekannter Weise, z. B. durch Verkochen mit verdünnter Mineralsäure, abspaltet. Geeignete i-Acylaminonaphthaline sind z. B. das i-Formyl-, -Acetyl-, -Propionyl- oder Benzoylaminonaphthalin. Als Halogensulfonsäure kommt vor allem Chlorsulfonsäure in Betracht.Process for the preparation of 1-aminonaphthalene-5-sulfonic acid amides It has been found that i-aminonaphthalene-5-sulfonic acid amides can be obtained in a simple manner obtained when i-acylaminonaphthalenes are used at an ordinary or moderately elevated temperature treated with excess halosulfonic acid, the i-acylaminonaphthalene-5-sulfonic acid halides thus obtained with ammonia, primary or secondary amines or their salts with weak acids, z. B. their carbonates or acetates, and finally the acyl group in in a manner known per se, for. B. by boiling with dilute mineral acid, split off. Suitable i-acylaminonaphthalenes are, for. B. the i-formyl-, -acetyl-, -propionyl- or benzoylaminonaphthalene. The main halogen sulfonic acid used is chlorosulfonic acid into consideration.

Die erhaltenen i-Aminonaphthalin-5-sulfonsäureamide sind wertvolle Zwischenprodukte für die Herstellung von Farbstoffen und Kunstharzen.The i-aminonaphthalene-5-sulfonic acid amides obtained are valuable Intermediate products for the manufacture of dyes and synthetic resins.

Man hat das i-Aminonaphthalin-5-sulfonsäureamid bisher durch Reduktion des 5-Nitronaphthalin-5-sulfonsäureamids mit überschüssiger jodwasserstoffsäure hergestellt. Diesem Verfahren gegenüber hat das vorliegende den Vorteil, daß es von leichter zugänglichen Ausgangsstoffen ausgeht und nur mit technisch üblichen Chemikalien arbeitet.The i-aminonaphthalene-5-sulfonic acid amide has so far been obtained by reduction of 5-nitronaphthalene-5-sulfonic acid amide with excess hydroiodic acid manufactured. In relation to this procedure, the present the Advantage that it starts from more easily accessible starting materials and only with technical usual chemicals works.

Die im folgenden Beispiel angegebenen Teile sind Gewichtsteile. Beispiel 185 Teile i-Acetylaminonaphthalin werden unter Kühlung und Rühren allmählich in 85o Teile Chlorsulfonsäure eingetragen. Man erwärmt das Reaktionsgemisch dann einige Zeit auf etwa 5o bis 6o° und gießt die klare Lösung schließlich auf Eis, wobei das i-Acetylaminonaphthalin-5-sulfonsäurechlorid als gelbliche, kristalline Masse ausfällt. Es kristallisiert aus Benzol in gelben Nadeln, die bei etwa 18o° unter Zersetzung schmelzen.The parts given in the following example are parts by weight. example 185 parts of i-acetylaminonaphthalene are gradually added with cooling and stirring 85o parts of chlorosulfonic acid entered. The reaction mixture is then warmed for a few times Time to about 5o to 6o ° and finally pour the clear solution onto ice, whereby the i-Acetylaminonaphthalene-5-sulfonic acid chloride precipitates as a yellowish, crystalline mass. It crystallizes from benzene in yellow needles that decompose at around 180 ° melt.

Der rohe, noch feuchte Preßkuchen des Sulfochlorids wird mit Zoo Teilen technischem Ammoniumcarbonat verrieben. Man überläßt das Gemisch einige Zeit sich selbst und verrührt es dann bei 5o bis 6o° mit 5oo Teilen Wasser. Nach etwa 2 bis 3 Stunden läßt man das Gemisch erkalten und saugt den Niederschlag ab. Man erhält 235 Teile einer krümeligen Masse, die aus praktisch reinem i-Acetylaminonaphthalin-5-sulfonsäureamid besteht. Nach dem Umkristallisieren aus verdünnter Essigsäure schmilzt es bei 23Z°.The raw, still moist press cake of the sulfochloride is made with Zoo parts triturated technical ammonium carbonate. The mixture is left to stand for a while himself and then stirred it at 5o to 6o ° with 500 parts of water. After about 2 to The mixture is allowed to cool for 3 hours and the precipitate is filtered off with suction. You get 235 parts of a crumbly mass consisting of practically pure i-acetylaminonaphthalene-5-sulfonic acid amide consists. After recrystallization from dilute acetic acid, it melts at 23 °.

Durch Kochen mit verdünnter Mineralsäure wird der Acetylrest in an sich bekannter Weise abgespalten. Durch Neutralisation der sauren Verseifungslösung erhält man das reine i-Aminonaphthalin-5-sulfonsäureamid vom Schmelzpunkt 259°. Es ist sowohl in Alkalien wie in verdünnten Mineralsäuren gut löslich.Boiling with dilute mineral acid turns the acetyl residue into split off in a known manner. By neutralizing the acidic saponification solution the pure i-aminonaphthalene-5-sulfonic acid amide with a melting point of 259 ° is obtained. It is readily soluble in both alkalis and dilute mineral acids.

Claims (1)

!-ATENTANSPPL'CH-. Verfahren zur Herstellung von i-Aminonaphthalin-5-sulfonsäureamiden, dadurch gekennzeichnet, daß man Z Acylaminonaphthaline mit Halogensulfonsäuren behandelt, die entstandenen i - Acylaminonaphthalin - 5 - sulfonsäurehalogenide mit Ammoniak, primären oder sekundären Aminen oder ihren Salzen mit schwachen Säuren umsetzt und schließlich in an sich bekannter Weise die Acylgruppe abspaltet. Angezogene Druckschriften: Berichte der deutschen chemischen Gesellschaft, Bd. 23, S. 1118.! -ATENTANSPPL'CH-. Process for the preparation of i-aminonaphthalene-5-sulfonic acid amides, characterized in that Z acylaminonaphthalenes are treated with halosulfonic acids, the resulting i - acylaminonaphthalene - 5 - sulfonic acid halides with ammonia, primary or secondary amines or their salts with weak acids and reacts finally splitting off the acyl group in a manner known per se. Referred publications: Reports of the German Chemical Society, Vol. 23, p. 1118.
DEB6947D 1942-08-07 1942-08-07 Process for the preparation of 1-aminonaphthalene-5-sulfonic acid amides Expired DE858555C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB6947D DE858555C (en) 1942-08-07 1942-08-07 Process for the preparation of 1-aminonaphthalene-5-sulfonic acid amides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB6947D DE858555C (en) 1942-08-07 1942-08-07 Process for the preparation of 1-aminonaphthalene-5-sulfonic acid amides

Publications (1)

Publication Number Publication Date
DE858555C true DE858555C (en) 1952-12-08

Family

ID=6954992

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB6947D Expired DE858555C (en) 1942-08-07 1942-08-07 Process for the preparation of 1-aminonaphthalene-5-sulfonic acid amides

Country Status (1)

Country Link
DE (1) DE858555C (en)

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
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