CH194685A - Process for the preparation of sulfanilic acid-4-dimethyl-aminoanilide. - Google Patents
Process for the preparation of sulfanilic acid-4-dimethyl-aminoanilide.Info
- Publication number
- CH194685A CH194685A CH194685DA CH194685A CH 194685 A CH194685 A CH 194685A CH 194685D A CH194685D A CH 194685DA CH 194685 A CH194685 A CH 194685A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- aminoanilide
- sulfanilic acid
- acid
- preparation
- 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-4-dimethyl-aminoanllid. 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- säurehalogeniden auf aromatische Diamine oder auf Monoacylverbindungen von aroma tischen Diaminen und naehherige Abspal tung der Acylgruppe oder durch Umsetzung von Acylsulfanilsäurehalogeniden mit aroma tischen Nitroaminen, Reduktion und Abspal tung der Acylgruppe.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von Sulfanil- säure-4-dimethyl-aminoanilid, welches da durch gekennzeichnet ist, dass man ein Acyl- sulfanilsäurehalogenid auf 4-,Aminodimethyl- anilin einwirken lässt und im so erhaltenen Produkt die Acylgruppe abspaltet.
Das, Sulfanilsäure-4-dimethyl-aminoani- lid schmilzt bei 231 bis- <B>232'</B> C. Es ist ziem lich schwer löslich in Alkohol und Methyl- alkohol und löst sich leicht in. Säuren und Laugen. Die neue Verbindung soll als Arz neimittel verwendet werden.
<I>Beispiel:</I> 60 Teile 4-Aminodimethylanilin werden in wässeriger Lösung mit 200 Teilen rohem, feuchten Propionylsulfanilsäurechlorid ge mischt und nach und nach ein Überschuss von Natronlauge zugegeben.
Die alkalische Lö sung wird filtriert und .das Kondensations produkt durch Zusatz von :Säure zur Ab scheidung gebracht. Zur Ab-bpaltung der Acetylgruppe wird es mit 500 Teilen, 15 % - igerSalzsäure gekocht. Die entstandene klare Lösung des Hydrochlorids wird neutralisiert, wobei das Sulfanilsäure-4-dimethyl-amino- anilid ausfällt.
Process for the preparation of sulfanilic acid-4-dimethyl-amino-amide. It has been found that anilides of sulf-a.nilic acid from aromatic diamines have an excellent effect 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 group or by reaction of acylsulfanilic acid halides with aromatic nitroamines, reduction and cleavage of the acyl group.
The present patent relates to a process for the preparation of sulfanilic acid 4-dimethylaminoanilide, which is characterized in that an acylsulfanilic acid halide is allowed to act on 4-, aminodimethylaniline and the acyl group is split off in the product thus obtained.
The, sulfanilic acid-4-dimethyl-aminoanilid melts at 231 to- <B> 232 '</B> C. It is not very soluble in alcohol and methyl alcohol and easily dissolves in acids and alkalis. The new compound is intended to be used as a drug.
<I> Example: </I> 60 parts of 4-aminodimethylaniline are mixed in aqueous solution with 200 parts of crude, moist propionylsulfanilic acid chloride and an excess of sodium hydroxide solution is gradually added.
The alkaline solution is filtered and the condensation product separated by adding: acid. To split off the acetyl group, it is boiled with 500 parts of 15% hydrochloric acid. The resulting clear solution of the hydrochloride is neutralized, whereby the sulfanilic acid 4-dimethylamino anilide precipitates.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH191673T | 1936-05-28 | ||
CH194685T | 1936-05-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH194685A true CH194685A (en) | 1937-12-15 |
Family
ID=25722158
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH194685D CH194685A (en) | 1936-05-28 | 1936-05-28 | Process for the preparation of sulfanilic acid-4-dimethyl-aminoanilide. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH194685A (en) |
-
1936
- 1936-05-28 CH CH194685D patent/CH194685A/en unknown
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CH194685A (en) | Process for the preparation of sulfanilic acid-4-dimethyl-aminoanilide. | |
CH194684A (en) | Process for the preparation of sulfanilic acid-3-aminoanilide. | |
CH194683A (en) | Process for the preparation of sulfanilic acid 2-methyl-5-aminoanilide. | |
CH194681A (en) | Process for the preparation of sulfanilic acid-4-aminoanilide. | |
CH191673A (en) | Process for the preparation of sulfanilic acid-4-aminoanilide. | |
CH199683A (en) | Process for the preparation of sulfanilic acid-4-aminoanilide. | |
CH194682A (en) | Process for the preparation of sulfanilic acid-4-aminoanilide. | |
CH199684A (en) | Process for the preparation of sulfanilic acid-3-aminoanilide. | |
CH195177A (en) | Process for the preparation of sulfanilic acid-4-aminoanilide. | |
AT112135B (en) | Process for the preparation of basic oxime ethers and their salts. | |
DE424659C (en) | Process for the preparation of methylaminoaceto-catechol dibenzyl ether | |
CH199910A (en) | Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. | |
CH199682A (en) | Process for the preparation of sulfanilic acid-4-aminoanilide. | |
DE513205C (en) | Process for the preparation of derivatives of the aminoarylantimony compounds | |
CH119151A (en) | Process for the production of a new intermediate product in the dye industry. | |
CH199685A (en) | Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. | |
CH194680A (en) | Process for the preparation of sulfanilic acid-4-amino-anilide. | |
CH222074A (en) | Process for the preparation of a sulfonamide. | |
CH198052A (en) | Process for the preparation of a quaternary aminoacetic acid amide derivative. | |
CH194885A (en) | Process for the preparation of sulfanilic acid-4-aminoanilide. | |
CH204379A (en) | Process for the production of the azo protein from mercury dianiline and serum protein. | |
CH215336A (en) | Process for the preparation of an aminoarylsulfoxide. | |
CH193611A (en) | Process for the preparation of a condensation product which can be used for pest control. | |
CH119152A (en) | Process for the production of a new intermediate product in the dye industry. | |
CH96297A (en) | Procedure for the presentation of a new medicinal product. |