CH194680A - Process for the preparation of sulfanilic acid-4-amino-anilide. - Google Patents
Process for the preparation of sulfanilic acid-4-amino-anilide.Info
- Publication number
- CH194680A CH194680A CH194680DA CH194680A CH 194680 A CH194680 A CH 194680A CH 194680D A CH194680D A CH 194680DA CH 194680 A CH194680 A CH 194680A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- sulfanilic acid
- anilide
- preparation
- acid
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Sulfanilsäure-4-amino-anilid. Es wurde gefunden, dass Anilide der Sulfanilsäure 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 zum Beispiel durch Einwirkung von Acetylsulfanilsäurehalogeniden auf aroma tische Diamine oder auf Monoacetylverbin- dungen von aromatischen Diaminen und nachherige Abspaltung der Acetylgruppe oder durch Umsetzung von Acetylsulfanil- sKurehalogeniden mit aromatischen Nitro- aminen,
Reduktion und Abspaltung der Ace- tylgruppe.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von Sulfanil- säure-4-a.mino-anili.d, welches dadurch ge kennzeichnet ist, dass man ein Acetylsulf- anilsäurehalogenid auf p-Phenylendiamin unter Zusatz von Natronlauge einwirken lässt und das entstandene p-Acetaminosulfo- nyl-p-phenylendiamin veriseift. Das iSulfanil@säure-4-amino-anilid ist bis jetzt noch nicht
bekannt. Es kristallisiert in langen, dünnen Nadeln, die bei 138 schmel zen. In kaltem Wasser ist es schwer, in heissem Wasser leichter löslich, ziemlich lös lich ist es in Alkohol und Methylalkohol, leicht löst es sich in Säuren und Laugen.
Es soll als, Arzneimittel verwendet wer den.
Beispiel: 50 Teile rohes, feuchtes Acetylsulfanil- säurechlorid (hergestellt aus: Acetanilid und Chlamulfonsäure) werden auf 70 Teile p- Phenylendiamin unter Zusatz von Natron lauge einwirken gelassen. Dann neutralisiert man mit Salzsäure und saugt das ausgefal lene p-Acetaminosulfonyl-p-phenylendiamin ab.
Man verseift es durch Kochen mit 15 % - iger Salzeäure. Das, in, geringer Menge als Nebenprodukt entstandene schwer lösliche Hydrochlorid des Diamids wird abfiltriert und das Filtrat mit Ammoniak versetzt. Das auskristallisierte Sulfanilsäure-4-aäninoani- lid wird abgesaugt und aus Wasser um kristallisiert.
Process for the preparation of sulfanilic acid-4-amino-anilide. 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 diamines were not previously known.
They are produced, for example, by the action of acetylsulfanilic acid halides on aromatic diamines or on monoacetyl compounds of aromatic diamines and subsequent cleavage of the acetyl group or by the reaction of acetylsulfanil-cure halides with aromatic nitroamines,
Reduction and elimination of the acetyl group.
The subject of the present patent is a process for the preparation of sulfanilic acid-4-a.mino-anili.d, which is characterized in that an acetylsulfanilic acid halide is allowed to act on p-phenylenediamine with the addition of sodium hydroxide solution and the resulting p -Acetaminosulfonyl-p-phenylenediamine saponified. The iSulfanil @ acid-4-amino-anilide is not yet
known. It crystallizes in long, thin needles that melt at 138. It is difficult to dissolve in cold water, more easily soluble in hot water, it is fairly soluble in alcohol and methyl alcohol, and it dissolves easily in acids and alkalis.
It is intended to be used as a medicinal product.
Example: 50 parts of crude, moist acetylsulfanilic acid chloride (made from: acetanilide and chlamulfonic acid) are allowed to act on 70 parts of p-phenylenediamine with the addition of sodium hydroxide solution. It is then neutralized with hydrochloric acid and the precipitated p-acetaminosulfonyl-p-phenylenediamine is filtered off with suction.
It is saponified by boiling with 15% hydrochloric acid. The sparingly soluble hydrochloride of diamide, which is formed as a by-product in a small amount, is filtered off and ammonia is added to the filtrate. The 4-aeninoanilide that has crystallized out is filtered off with suction and recrystallized from water.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE194680X | 1936-03-21 | ||
CH191673T | 1936-05-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH194680A true CH194680A (en) | 1937-12-15 |
Family
ID=25722162
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH194680D CH194680A (en) | 1936-03-21 | 1937-03-17 | Process for the preparation of sulfanilic acid-4-amino-anilide. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH194680A (en) |
-
1937
- 1937-03-17 CH CH194680D patent/CH194680A/en unknown
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