CH199910A - Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. - Google Patents
Process for the preparation of N-methylsulfanilic acid-4-aminoanilide.Info
- Publication number
- CH199910A CH199910A CH199910DA CH199910A CH 199910 A CH199910 A CH 199910A CH 199910D A CH199910D A CH 199910DA CH 199910 A CH199910 A CH 199910A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- aminoanilide
- methylsulfanilic
- preparation
- catalyst
- Prior art date
Links
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Darstellung von N-Nethylsulfanilsäure-4-aminoanilid. Es wurde gefunden, dass Anilide der Sulfanilsäure aus aromatischen Diaminen in vivo eine hervorragende Wirkung gegen Streptokokken aufweisen. Anilide der Sulf- anilsäure aus aromatischen Aminen waren bisher nicht bekannt.
Ihre Darstellung kann dadurch erfolgen, dass man Acylsulfanil- säurehalogenide auf aromatische Diamine oder Monoacylverbindungen von aromati schen Aminen einwirken lässt und die Acyl- gruppen abspaltet oder Acylsulfanilsäure- halogenide mit aromatischen Nitroaminen umsetzt, reduziert und die Acylgruppen ab spaltet.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von N-Methyl- sulfanilsäure-4-aminoanilid, welches dadurch gekennzeichnet ist, dass man ein p-Halogen- benzolsulfonsäure-4-acylaminoanilid mit Mo nomethylamin in Gegenwart von Katalysa toren, wie Naturkupfer oder Kupfersalzen, zum N-Methylsulfanilsäure-4-acylaminoani- lid umsetzt und die Acylgruppe abspaltet.
Das N-Methylsulfanilsäure-4-aminoanilid schmilzt bei 191 bis<B>192'.</B> Es ist unlöslich in kaltem und heissem Wasser, ziemlich lös lich. in Äthyl- und Methylalkohol, leicht lös lich in Mineralsäuren und Alkalilaugen. Die neue Verbindung soll als Arzneimittel ver wendet werden.
<I>Beispiel:</I> 6 Teile p-Chlorbenzolsulfonsäure-4-acet- aminoanilid (hergestellt aus p-Chlorbenzol- sulfochlorid und p-Aminoacetanilid, F. P. 201 bis 202 ), 0,5 Teile Naturkupfer C und 50 Teile 30%ige Monomethylaminlösung werden auf 170 bis 175 erhitzt, dann fügt man Natronlauge im Überschuss zu, filtriert und kocht 1/s Stunde. Die erkaltete Lösung wird nochmals filtriert und das Filtrat durch Säurezusatz neutralisiert.
Das rohe N-Methyl- sulfanilsäure-4-aminoanilid wird aus ver dünntem Methylalkohol umkristallisiert.
Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. It has been found that anilides of sulfanilic acid from aromatic diamines have an excellent effect against streptococci in vivo. Anilides of sulfanilic acid from aromatic amines were not previously known.
They can be prepared by letting acylsulfanilic acid halides act on aromatic diamines or monoacyl compounds of aromatic amines and splitting off the acyl groups or reacting acylsulfanilic acid halides with aromatic nitroamines, reducing them and splitting off the acyl groups.
The present patent is a process for the preparation of N-methylsulfanilic acid-4-aminoanilide, which is characterized in that one p-halobenzenesulfonic acid-4-acylaminoanilide with Monomethylamine in the presence of catalysts, such as natural copper or copper salts , converts to N-methylsulfanilic acid-4-acylaminoanilide and splits off the acyl group.
The N-methylsulfanilic acid-4-aminoanilide melts at 191 to <B> 192 '. </B> It is insoluble in cold and hot water, quite soluble. in ethyl and methyl alcohol, easily soluble in mineral acids and alkaline solutions. The new compound is intended to be used as a drug.
<I> Example: </I> 6 parts of p-chlorobenzenesulphonic acid-4-acet-aminoanilide (made from p-chlorobenzenesulphochloride and p-aminoacetanilide, FP 201 to 202), 0.5 parts of natural copper C and 50 parts of 30% ige monomethylamine solution are heated to 170 to 175, then sodium hydroxide solution is added in excess, filtered and boiled for 1 / s hour. The cooled solution is filtered again and the filtrate is neutralized by adding acid.
The crude N-methylsulfanilic acid 4-aminoanilide is recrystallized from dilute methyl alcohol.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH199910T | 1937-02-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH199910A true CH199910A (en) | 1938-09-15 |
Family
ID=4442066
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH199910D CH199910A (en) | 1937-02-19 | 1937-02-19 | Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH199910A (en) |
-
1937
- 1937-02-19 CH CH199910D patent/CH199910A/en unknown
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