CH221845A - Process for the preparation of the hexamethylenetetramine salt of 4-aminobenzenesulfonamide-phosphamic acid. - Google Patents
Process for the preparation of the hexamethylenetetramine salt of 4-aminobenzenesulfonamide-phosphamic acid.Info
- Publication number
- CH221845A CH221845A CH221845DA CH221845A CH 221845 A CH221845 A CH 221845A CH 221845D A CH221845D A CH 221845DA CH 221845 A CH221845 A CH 221845A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminobenzenesulfonamide
- phosphamic
- acid
- preparation
- phosphamic acid
- Prior art date
Links
Description
Verfahren zur Darstellung des Hegamethylentetraminsalzes der 4-Aminobenzolsulfonamid-phosphamidsäur e. Wie im Patent Nr. 211297 angegeben, ist, werden durch Erhitzen von 4-Aminobenzol- sulfonamiden mit Phosphoroxychlorid Phos- phorsäuredichloride dieser 4-Aminobenzol- sulfonamide erhalten, die sich durch Um setzung mit Laugen oder Aminen in stark bakterizid wirkende Phosphorsäuren bezw. Phosphamidsäuren umwandeln lassen.
Es wurde nun gefunden, dass man aus diesen Phosphorsäureabkömmlingen der 4- Aminobenzolsulfonamide besonders wertvolle bakterizide Verbindungen erhält, wenn man sie mit Alkaloiden oder andern therapeutisch verwendbaren Basen, wie zum Beispiel Chi- nolin- oder Acridinbasen zur Reaktion bringt.
Die Darstellung der neuen Verbindungen kann durch Neutralisation der Base mit einer 4-Aminobenzolsulfonamid-phosphamid- säure oder durch Umsetzung eines leicht löslichen Salzes einer geeigneten Base mit einem Salz einer 4-Aminobenzolsulfonamid- hhosphamidsäure erfolgen.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung des Hexa- methylentetraminsalzes der 4-Aminobenzol- sulfonamid-phosphamidsKure, welches da durch gekennzeichnet ist, dass 4-Aminobenzol- sulfonamid-phosphamidsäure auf Hexamethy- lentetramin einwirken gelassen wird.
An Stelle von Hexamethylentetramin und der freien 4-Aminobenzolsulf onamid-phosphamid- säure können auch deren leicht wasserlösliche Salze zur Umsetzung verwendet werden.
Das bisher unbekannte Hexamethylen- tetraminsalz der 4-Aminobenzolsulfonamid- phosphamidsäure zersetzt sich bei 202-203 . Es ist ziemlich schwer löslich in kaltem Wasser und soll als Arzneimittel dienen. <I>Beispiel 1:</I> 2 & Teile Hexamethylentetramin werden in 75 Teilen Wasser gelöst und 50 Teile frisch gefällte, feuchte 4-Aminobenzolsulfon- amid-phosphamidsäure (aus 62 Teilen kristal- lisiertem 4-a.minobenzolsulfonamid-phosph- amidsaurem Natrium) eingetragen.
Man schüttelt die -Mischung 10-15 Minuten, wo bei sich das 4-aminobenzolsulfonamid-phosph- amidsaure Hexamethylentetramin in körni gen Kristallen in annähernd quantitativer Ausbeute abscheidet. Es wird abgesaugt, mit wenig kaltem Wasser gewaschen und ge trocknet.
<I>Beispiel 2:</I> Man stellt aus 50 cm' 36 %igem Formalin und zirka 30 cm' 25%igem Ammoniak eine Lösung von Hexamethylentetramin her und trägt direkt oder nach Einengen auf 40 cm' 25 Teile frisch gefällte 4-Aminobenzolsulfon- amid-phosphamidsäure ein. Nach Beendigung der Umsetzung saugt man das Reaktionspro dukt ab. Man erhält das im Beispiel 1 be- schriebene 4-aminobenzolsulfonamid-phosph- amidsaure Hexamethylentetramin in guter Ausbeute.
Process for the preparation of the hegamethylenetetramine salt of 4-aminobenzenesulfonamide-phosphamic acid. As stated in patent no. 211297, these 4-aminobenzenesulfonamides are obtained by heating 4-aminobenzenesulfonamides with phosphorus oxychloride phosphoric acid dichlorides, which can be converted into strongly bactericidal phosphoric acids by reaction with alkalis or amines. Let convert phosphamic acids.
It has now been found that particularly valuable bactericidal compounds are obtained from these phosphoric acid derivatives of the 4-aminobenzenesulfonamides if they are reacted with alkaloids or other therapeutically useful bases, such as, for example, quinoline or acridine bases.
The new compounds can be prepared by neutralizing the base with a 4-aminobenzenesulphonamide-phosphamic acid or by reacting a readily soluble salt of a suitable base with a salt of a 4-aminobenzenesulphonamide-phosphamic acid.
The subject of the present patent is a process for the preparation of the hexamethylene tetramine salt of the 4-aminobenzenesulfonamide-phosphamidscure, which is characterized in that 4-aminobenzenesulfonamide-phosphamic acid is allowed to act on hexamethylene-tetramine.
Instead of hexamethylenetetramine and the free 4-aminobenzenesulfonamido-phosphamidic acid, their readily water-soluble salts can also be used for the reaction.
The previously unknown hexamethylene tetramine salt of 4-aminobenzenesulfonamide phosphamic acid decomposes at 202-203. It is quite sparingly soluble in cold water and is intended to be used as a medicine. <I> Example 1: </I> 2 & parts of hexamethylenetetramine are dissolved in 75 parts of water and 50 parts of freshly precipitated, moist 4-aminobenzenesulphonamide-phosphamic acid (from 62 parts of crystallized 4-a.minobenzenesulphonamide-phosphamic acid Sodium).
The mixture is shaken for 10-15 minutes, during which the 4-aminobenzenesulfonamide-phosphamic acid hexamethylenetetramine is deposited in granular crystals in an approximately quantitative yield. It is filtered off with suction, washed with a little cold water and dried.
<I> Example 2: </I> A solution of hexamethylenetetramine is prepared from 50 cm '36% formalin and about 30 cm' 25% ammonia and, either directly or after concentrating to 40 cm ', 25 parts of freshly precipitated 4- Aminobenzenesulfonamide-phosphamic acid. After the reaction has ended, the reaction product is suctioned off. The 4-aminobenzenesulphonamide-phosphamic acid hexamethylenetetramine described in Example 1 is obtained in good yield.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE221845X | 1938-07-29 | ||
| CH213147T | 1939-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH221845A true CH221845A (en) | 1942-06-15 |
Family
ID=25725374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH221845D CH221845A (en) | 1938-07-29 | 1939-06-27 | Process for the preparation of the hexamethylenetetramine salt of 4-aminobenzenesulfonamide-phosphamic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH221845A (en) |
-
1939
- 1939-06-27 CH CH221845D patent/CH221845A/en unknown
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