CH191673A - Process for the preparation of sulfanilic acid-4-aminoanilide. - Google Patents
Process for the preparation of sulfanilic acid-4-aminoanilide.Info
- Publication number
- CH191673A CH191673A CH191673DA CH191673A CH 191673 A CH191673 A CH 191673A CH 191673D A CH191673D A CH 191673DA CH 191673 A CH191673 A CH 191673A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminoanilide
- sulfanilic acid
- preparation
- acid
- sulfanilic
- 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
Description
Verfahren zur Darstellung von Sulfanilsäure-4-aminoanilid. Es wurde gefunden, dass Anilide der Sul- fanilsäure aus aromatischen Diaminen in vivo eine hervorragende Wirkung gegen Strepto- kokken aufweisen. Anilide der Sulfanilsäure aus aromatischen Diaminen waren bisher nicht bekannt.
Ihre Herstellung erfolgt durch Ein wirkung von Acylsulfanilsäurehalogeniden auf aromatische Diamine oder auf Monoäcylver- bindungen von aromatischen Diaminen und nachheriger Abspaltung der Acylgruppen oder durch Umsetzung von Acylsulfanilsäurehaloge- niden mit aromatischen Nitroaminen, Reduk tion und Abspaltung der 'Acylgruppe.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von Sulfanil- säure-4-aminoanilid, welches dadurch gekenn zeichnet ist, dass man Acylsulfanilsäurehaloge- nid auf Monoacyl-p-phenylendiamin einwirken lässt und die Acylgruppen abspaltet.
Das Sulfanilsäure-4-aminoanilid schmilzt bei 138 . Es ist ziemlich löslich in Alkohol und Methylalkohol und löst sich leicht in Säuren und Laugen. Die neue Verbindung soll als Arzneimittel verwendet werden.
<I>Beispiel:</I> <B>150</B> Teile Monoacetyl-p-phenylendiamin werden in 300 Teilen Methylalkohol mit der berechneten Menge von rohem, feuchtem Ace- tylsulfanilsäurechlorid unter Zusatz von Na tronlauge zur Reaktion gebracht. Dann gibt man 500 Teile Wasser und Natronlauge im Überschuss zu und filtriert das nicht umge setzte Monoacetyl-p-phenylendiamin ab. Das Filtrat wird angesäuert und das Kondensa tionsprodukt abgesaugt. Zur Abspaltung der Acetylgruppen wird es 1 Stunde mit 700 Tei len 15 o/oiger Salzsäure gekocht.
Die eDt- standene klare Lösung des Hydrochlorids wird neutralisiert und das Sulfanilsäure-4- aminoanilid unter Zusatz von Kohle aus Was ser umkristallisiert.
Process for the preparation of sulfanilic acid-4-aminoanilide. It has been found that anilides of sulphanilic acid from aromatic diamines have an excellent action against streptococci in vivo. Anilides of sulfanilic acid from aromatic diamines were not previously known.
They are produced by the action of acylsulfanilic acid halides on aromatic diamines or on monoacyl compounds of aromatic diamines and subsequent cleavage of the acyl groups or by reaction of acylsulfanilic acid halides with aromatic nitroamines, reduction and cleavage of the acyl group.
The subject of the present patent is a process for the preparation of sulfanilic acid-4-aminoanilide, which is characterized in that acylsulfanilic acid halide is allowed to act on monoacyl-p-phenylenediamine and the acyl groups are split off.
The sulfanilic acid 4-aminoanilide melts at 138. It is quite soluble in alcohol and methyl alcohol, and easily dissolves in acids and alkalis. The new compound is intended to be used as a medicine.
<I> Example: </I> <B> 150 </B> parts of monoacetyl-p-phenylenediamine are reacted in 300 parts of methyl alcohol with the calculated amount of crude, moist acetylsulfanilic acid chloride with the addition of sodium hydroxide solution. Then 500 parts of water and sodium hydroxide solution are added in excess and the unconverted monoacetyl-p-phenylenediamine is filtered off. The filtrate is acidified and the condensation product is filtered off with suction. To split off the acetyl groups, it is boiled with 700 parts of 15% hydrochloric acid for 1 hour.
The resulting clear solution of the hydrochloride is neutralized and the sulfanilic acid-4-aminoanilide is recrystallized from water with the addition of charcoal.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH191673T | 1936-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH191673A true CH191673A (en) | 1937-06-30 |
Family
ID=4437760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH191673D CH191673A (en) | 1936-05-28 | 1936-05-28 | Process for the preparation of sulfanilic acid-4-aminoanilide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH191673A (en) |
-
1936
- 1936-05-28 CH CH191673D patent/CH191673A/en unknown
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