CH209121A - Process for preparing a sulfonic acid amide compound. - Google Patents
Process for preparing a sulfonic acid amide compound.Info
- Publication number
- CH209121A CH209121A CH209121DA CH209121A CH 209121 A CH209121 A CH 209121A CH 209121D A CH209121D A CH 209121DA CH 209121 A CH209121 A CH 209121A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonic acid
- methylbenzene
- amide compound
- acid amide
- compound
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer Sulfonsäureamidverbindung. Das Hauptpatent betrifft ein Verfahren zur Darstellung einer therapeutisch wertvollen Sulfonsäureamidverbindung. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer Sulfonsäureamidverbindung, dadurch gekennzeichnet, dass man 1-Acyl- amino-2-methoxy-5-methylbenzol durch Ein wirken von Chlorsulfonsäure in 1-Acylamino-2- methoxy-5-methylbenzol-4-sulfonsäurechlorid überführt,
diese Verbindung durch Einwirken von Konoinethylamin in 1-Acylamino-2 methoxy-5-inethylbenzol-4-sulfonsäuremono- methylamid überführt und aus dieser 'Ver bindung die Acylgruppe durch Verseifung abspaltet.
Das so erhältliche 1-Amino-2-methoxy-5- methylbenzol- 4 - sulfonsäuremonomethylamid bildet farblose Kristalle vom Schmelzpunkt 139 0. Es soll therapeutische Anwendung finden.
<I>Beispiel:</I> 100 g 1-Acetylamino-2-methoxy-5-methyl- benzol (aus Benzol weisse Kristalle vom Schmelzpunkt 1120) werden bei 20 0 in 300 cm' Chlorsulfonsäure eingetragen. Die Mischung wird anschliessend 4 Stunden auf 70 0 erhitzt. Sodann wird in Eiswasser ein gerührt und das ausgefällte 1-Acetylamino-2- methoxy-5-methylbenzol-4-sulfousäurechlorid abgesaugt. Es bildet nach dem Umkristalli- sieren aus wässrigem Aceton farblose Kristalle vom Schmelzpunkt 135 0.
Zur Überführung in das Monomethyla.mid wird das von über schüssiger Mineralsäure durch 'Auswaschen befreite, noch feuchte Chlorid in 400 cm-' Wasser und mindestens 2 Mol Monomethyl- amin angeschlämmt und 30 Minuten bei 60 bis 70 0 gerührt.
Nach dem Abkühlen wird das 1-Acetylamino-2-methoxy.5.methylbenzol- 4-sulfonsäuremonomethylamid abgesaugt und durch Umlösen aus Natronlauge und Am moniumchlorid gereinigt. 50 g dieser Ver- bindung werden mit 250 cm3 20 %iger Natron- lauge unter Rühren gekocht.
Aus der Mi schung wird das entstandene 1-Amino-2- methoxy- 5 -methylb enzol-4- sulfonsäuremon o- methylamid nach dem Erkalten durch Ab stumpfen des Alkalis mit Essigsäure oder Ammoniumchlorid ausgefällt. Es bildet nach dem Umkristallisieren aus verdünntem Alko hol farblose Kristalle vorn Schmelzpunkt 139 .
Process for preparing a sulfonic acid amide compound. The main patent relates to a process for the preparation of a therapeutically useful sulfonic acid amide compound. The subject of the present patent is a process for the preparation of a sulfonic acid amide compound, characterized in that 1-acyl-amino-2-methoxy-5-methylbenzene by an action of chlorosulfonic acid in 1-acylamino-2-methoxy-5-methylbenzene-4- sulfonic acid chloride transferred,
this compound is converted into 1-acylamino-2-methoxy-5-ynethylbenzene-4-sulfonic acid monomethylamide by the action of konoinethylamine and the acyl group is split off from this compound by saponification.
The 1-amino-2-methoxy-5-methylbenzene-4-sulfonic acid monomethylamide obtainable in this way forms colorless crystals with a melting point of 139 0. It is said to be of therapeutic use.
<I> Example: </I> 100 g of 1-acetylamino-2-methoxy-5-methylbenzene (white crystals from benzene with a melting point of 1120) are introduced into 300 cm of chlorosulfonic acid at 20 °. The mixture is then heated to 70 ° for 4 hours. It is then stirred into ice water and the 1-acetylamino-2-methoxy-5-methylbenzene-4-sulfous acid chloride which has precipitated is filtered off with suction. After recrystallization from aqueous acetone, it forms colorless crystals with a melting point of 135 °.
To convert the excess mineral acid into the Monomethyla.mid, the still moist chloride, freed from excess mineral acid, is suspended in 400 cm- 'of water and at least 2 mol of monomethylamine and stirred at 60 to 70 ° for 30 minutes.
After cooling, the 1-acetylamino-2-methoxy.5.methylbenzene-4-sulfonic acid monomethylamide is filtered off with suction and purified by dissolving it from sodium hydroxide solution and ammonium chloride. 50 g of this compound are boiled with 250 cm3 of 20% sodium hydroxide solution while stirring.
The resulting 1-amino-2-methoxy-5-methylbenzene-4-sulfonic acid mono-methylamide is precipitated from the mixture after cooling by blunting the alkali with acetic acid or ammonium chloride. After recrystallization from dilute alcohol, it forms colorless crystals with a melting point of 139.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE209121X | 1937-03-04 | ||
CH203550T | 1938-02-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH209121A true CH209121A (en) | 1940-03-15 |
Family
ID=25723944
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH209121D CH209121A (en) | 1937-03-04 | 1938-02-22 | Process for preparing a sulfonic acid amide compound. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH209121A (en) |
-
1938
- 1938-02-22 CH CH209121D patent/CH209121A/en unknown
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