CH255624A - Process for the preparation of an aromatic acylsulfonamide. - Google Patents
Process for the preparation of an aromatic acylsulfonamide.Info
- Publication number
- CH255624A CH255624A CH255624DA CH255624A CH 255624 A CH255624 A CH 255624A CH 255624D A CH255624D A CH 255624DA CH 255624 A CH255624 A CH 255624A
- Authority
- CH
- Switzerland
- Prior art keywords
- reaction
- aromatic
- act
- compound
- dependent
- 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
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines aromatischen Acylsulfonamids. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines aromatischen Aevlsulfonamids. Das Verfahren ist dadurch gekennzeichnet, da.ss man eine Verbindung der Formel
EMI0001.0008
# au f eine Verbindung der Formel
EMI0001.0016
worin X und Y zwei reaktionsfähige,
bei der Reaktion mit Ausnahme einer in einem von ihnen enthaltenen NH-Gruppe sich ab- paltende Reste bedeuten, einwirken lässt.
Die entstandene neue Verbindung, das N - (f '- Naphthoyl) - p - toluolsulf onamid, schmilzt bei 166--168 und soll als Desinfek tionsmittel', z. B. für Gebrauchsgegenstände, V < ,rwendung finden.
Beispiel r: 17,1 Teile p-Toluolsulfonamid werden in 100 Teilen Nitrobenzol suspendiert und mit 19 Teilen Aluminiumchlorid und 19 Teilen ss-Nnphthoesä,urechlorid versetzt. Das Ge misch wird 2 Stunden auf 50 erwärmt und hierauf das Lösungsmittel mit Wasserdampf abdestilliert. Der Rückstand wird in Soda lösung aufgenommen, mit Tierkohle behan delt und filtriert. Aus dem Filtrat wird das N - (f3 - Naphthoyl) - p - toluolsulfonamid mit.
Essigsäure ausgefällt und durch Umkristal- lisieren aus Alkohol gereinigt.
Statt unter Zuhilfenahme eines Konden- sationsmittels kann die Reaktion auch in Gegenwart eines säurebindenden Mittels, wie z. B. von Pyridin oder Dimethylanilin, oder in Gegenwart eines Katalysators, wie z. B. von Kupferpulver, ausgeführt werden.
An Stelle eines, Halogenids kann auch die freie ss-Naphthoesäure in Gegenwart eines Kondensationsmittels, wie Phospharpentogyd oder Phosphorpentachlorid, verwendet werden. <I>Beispiel 2:</I> 28,6 Teile ss-Naphthoesäureamid werden in 200 Teilen absolutem Xylol gelöst. Dann fügt man 8 Teile Natriumamid hinzu und erwärmt bis zum Aufhören der Ammoniak entwicklung.
Nach dem Abkühlen gibt man 38 Teile p-To.luolsulfochlorid in<B>100</B> Teilen Xylol zu und erhitzt mehrere Stunden unter Rückfloss. Nach beendeter Reaktion wird das Xylol im Vakuum abdestilliert. Der Rück stand wird in Bikarbona,tlösung aufgenom men, mit Tierkohle behandelt, filtriert und durch Ansäuern ausgefällt. Das N-(ss-Naph- thGyl)-p-toluol'sulf onamid wird aus verdünn tem Alkohol umkristallisiert und so völlig rein erhalten.
Process for the preparation of an aromatic acylsulfonamide. The present patent relates to a process for the preparation of an aromatic sulfonamide. The process is characterized in that a compound of the formula
EMI0001.0008
# to a compound of the formula
EMI0001.0016
where X and Y are two reactive,
in the reaction, with the exception of an NH group contained in one of them, means splitting off radicals, can act.
The resulting new compound, the N - (f '- naphthoyl) - p - toluenesulfonamide, melts at 166-168 and is said to be used as a disinfectant', e.g. B. for everyday objects, V <, find application.
Example r: 17.1 parts of p-toluenesulfonamide are suspended in 100 parts of nitrobenzene, and 19 parts of aluminum chloride and 19 parts of ß-Nnphthoic acid chloride are added. The mixture is heated to 50 for 2 hours and the solvent is then distilled off with steam. The residue is taken up in soda solution, treated with animal charcoal and filtered. The N - (f3 - naphthoyl) - p - toluenesulfonamide is formed from the filtrate.
Acetic acid precipitated and purified by recrystallization from alcohol.
Instead of using a condensation agent, the reaction can also be carried out in the presence of an acid-binding agent, such as B. of pyridine or dimethylaniline, or in the presence of a catalyst, such as. B. of copper powder.
Instead of a halide, it is also possible to use the free β-naphthoic acid in the presence of a condensing agent such as phospharpentogide or phosphorus pentachloride. Example 2: 28.6 parts of β-naphthoic acid amide are dissolved in 200 parts of absolute xylene. Then 8 parts of sodium amide are added and the mixture is heated until the evolution of ammonia ceases.
After cooling, 38 parts of p-To.luolsulfochlorid in 100 parts of xylene are added and the mixture is heated under reflux for several hours. After the reaction has ended, the xylene is distilled off in vacuo. The residue is taken up in bicarbonate solution, treated with animal charcoal, filtered and precipitated by acidification. The N- (ss-NaphthGyl) -p-toluene sulfonamide is recrystallized from dilute alcohol and thus obtained completely pure.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH249867T | 1944-10-25 | ||
CH255624T | 1944-10-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH255624A true CH255624A (en) | 1948-06-30 |
Family
ID=25729400
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH255624D CH255624A (en) | 1944-10-25 | 1944-10-25 | Process for the preparation of an aromatic acylsulfonamide. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH255624A (en) |
-
1944
- 1944-10-25 CH CH255624D patent/CH255624A/en unknown
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