CH194684A - Process for the preparation of sulfanilic acid-3-aminoanilide. - Google Patents
Process for the preparation of sulfanilic acid-3-aminoanilide.Info
- Publication number
- CH194684A CH194684A CH194684DA CH194684A CH 194684 A CH194684 A CH 194684A CH 194684D A CH194684D A CH 194684DA CH 194684 A CH194684 A CH 194684A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminoanilide
- acid
- preparation
- sulfanilic acid
- acyl
- 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)
Description
Verfahren zur Darstellung von Sulfanilsäure-3-aminoanilid. Es wurde gefunden, dass Anilide -der Sulf- a.nilsäure aus aromatischen Diaminen in vivo eine hervorragende Wirkung gegen Streptokokken aufweisen. Anilide der Sulf- anilsäure aus, aromatischen Diaminen waren bisher nicht bekannt.
Ihre Herstellung er folgt durch Einwirkung von Acylsulfanil- säurehalogeni4en auf aromatische Diamine oder auf Monoacylverbindungen von aroma tischen Diaminen und nachherige Abspal tung der Acylgruppe oder durch Umsetzung von Acylsulfanileäurehalogeniden mit aro matischen Nitroaminen, Reduktion und Ab spaltung der Acylgruppe.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von Sulfanil- säure-3-aminoanilid, welches dadurch ge kennzeichnet ist, :dass man ein Acylsulfanil- säurehalogenid auf ein Mono-acyl-meta-phe- nylendiamin einwirken lässt und im so er haltenen Produkt .die Acylgruppen abspaltet.
Das Sulfanilsäure-.3-aminoanilid schmilzt bei 158 bis<B>160'.</B> Es ist ziemlich löslich in Alkohol und Methylalkohol und löst sich leicht in Säuren und Laugen. Die neue Ver bindung soll als Arzneimittel verwendet werden.
<I>Beispiel;</I> 40 Teile Monoacetyl-m-phenylendiamin- hydrochlorid werden in wässeriger Lösung mit @d-er berechneten Menge von rohem, feuchtem Acetylsulfanilsäurechlorid versetzt. Durch langsamen Zusatz von verdünnter Natronlauge wird die Kondensation bewirkt. Die alkalische Lösung wird filtriert und das Kondensationsprodukt @dureh Säurezusatz ausgefällt.
Das Acetylsulfanilsäure-3-acetyl- aminoanilid wird zur Abspaltung .der Ace- tylgruppen mit 2.50 Teilen 15 % iger Salz säure gekocht. Die Lösung des, Hydrochlo- rids wird neutralisiert, das auskristallisie rende Sulfanilsäure-3-aminoanilid abgesaugt und auG Wasser umkristallisiert.
Process for the preparation of sulfanilic acid-3-aminoanilide. It has been found that anilides -der sulf-a.nilic acid from aromatic diamines have an excellent action against streptococci in vivo. Anilides of sulphanilic 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 group 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-3-aminoanilide, which is characterized in that: an acylsulfanilic acid halide is allowed to act on a mono-acyl-meta-phenylenediamine and in the product obtained in this way . splits off the acyl groups.
The sulfanilic acid .3-aminoanilide melts at 158 to <B> 160 '. </B> It is quite soluble in alcohol and methyl alcohol and easily dissolves in acids and alkalis. The new connection is intended to be used as a drug.
<I> Example; </I> 40 parts of monoacetyl-m-phenylenediamine hydrochloride are mixed with the calculated amount of crude, moist acetylsulfanilic acid chloride in aqueous solution. The condensation is caused by the slow addition of dilute sodium hydroxide solution. The alkaline solution is filtered and the condensation product is precipitated from the addition of acid.
The acetylsulfanilic acid 3-acetylaminoanilide is boiled with 2.50 parts of 15% hydrochloric acid to split off the acetyl groups. The solution of the hydrochloride is neutralized, the sulfanilic acid 3-aminoanilide which crystallizes out is filtered off with suction and recrystallized from water.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH194684T | 1936-05-28 | ||
CH191673T | 1936-05-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH194684A true CH194684A (en) | 1937-12-15 |
Family
ID=25722157
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH194684D CH194684A (en) | 1936-05-28 | 1936-05-28 | Process for the preparation of sulfanilic acid-3-aminoanilide. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH194684A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001002350A2 (en) * | 1999-06-30 | 2001-01-11 | Bayer Aktiengesellschaft | Novel amino sulfonamides and amido sulfonamides as antiviral agents |
-
1936
- 1936-05-28 CH CH194684D patent/CH194684A/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001002350A2 (en) * | 1999-06-30 | 2001-01-11 | Bayer Aktiengesellschaft | Novel amino sulfonamides and amido sulfonamides as antiviral agents |
WO2001002350A3 (en) * | 1999-06-30 | 2001-03-29 | Bayer Ag | Novel amino sulfonamides and amido sulfonamides as antiviral agents |
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