CH301683A - Process for the preparation of a new aromatic thioether. - Google Patents
Process for the preparation of a new aromatic thioether.Info
- Publication number
- CH301683A CH301683A CH301683DA CH301683A CH 301683 A CH301683 A CH 301683A CH 301683D A CH301683D A CH 301683DA CH 301683 A CH301683 A CH 301683A
- Authority
- CH
- Switzerland
- Prior art keywords
- thioether
- compound
- formula
- isobutyl
- new aromatic
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
- A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Verfahren zur Herstellung eines neuen aromatischen</B> Thioäthers. Das vorliegende Patent bezieht sich auf ein Verfahren zur Herstellung eines neuen aroma tischen Thioäthers, nämlich des 2,4-Dioxy-5- sulfo-phenyl-isobutyl-thioäthers.
Dieser Thioäther hat eine starke Hemm wirkung auf das Bakterienwachstum sowie eine gewisse vermicide Wirkung und soll als Chemotherapeuticum Verwendung finden.
Das erfindungsgemässe Verfahren zur Her stellung des neuen aromatischen Thioäthers ist, dadurch gekennzeichnet, dass man auf eine Verbindung der Formel
EMI0001.0010
eine Verbindung der Formel
EMI0001.0011
einwirken lässt, wobei X und Y sich bei der Reaktion abspaltende Reste bedeuten, und dass man anschliessend im erhaltenen Thioäther mit einem Sulfurierungsmittel die Sulfogruppe einführt.
Man kann beispielsweise auf ein Metall salz des 2,4-Dioxy-thiophenols (X = Me, z. B. Natrium, Kalium usw.) eine Verbindung der Formel II einwirken lassen, in welcher Y ein Ilalogenatom oder einen andern sich leicht abspaltenden Rest, wie z. B. einen Alkyl- oder Ai_yl-sulfonyloxyrest, bedeutet. Es ist weiter auch möglich, dass 2,4-Dioxy-thiophenol in Ge- genwart eines basischen Kondensationsmittels mit einer Verbindung der Formel II umzuset zen.
Die Einführung der Sulfogruppe kann mit Hilfe von Oleum oder von Halogensulfon- säuren, wie z. B. Chlorsulfonsäure, erfolgen. , Der auf diese Weise erhaltene 2,4-Dioxy-5- sulfo-phenyl-isobutyl-thioäther bildet ein Na triumsalz, das in weissen Blättchen kristalli siert, die sich bei 325 unter Braunfärbung zersetzen.
Beispiel: 9,1 g Natrium werden in 500 cm 3 abs. Äthanol gelöst. Die Lösung wird mit 50 g 2,4- Dioxy-thiophenol versetzt und unter Rühren 50 g Isobutylbromid zugegeben. Man erwärmt 3 Stunden auf dem Dampfbad, destilliert das Äthanol ab, nimmt in Äther auf, behandelt die ätherische Lösung mit Wasser und destilliert sie dann nach dem Trocknen im Vakuum.
Der so erhaltene, unter 0,06 mm bei<B>113</B> bis<B>1150,</B> siedende 2,4-Dioxy-phenyl-isobutyl-thioäther (50 g) wird in 300 em3 abs. Nitrobenzol ge löst und unter Eiskühlung tropfenweise mit 30 g Chlorsulfonsäure versetzt. Man turbiniert 2 Stunden bei 18 bis 22 , lässt dann über Nacht stehen, schüttelt die Nitrobenzollösung mit Wasser aus und engt die wässrige Lösung im Vakuum auf 250 cms ein.
Zur Reinigung wird die Lösung nach dem Klären mit Tierkohle mit Natriumchlorid zwecks Fällung des Na triumsalzes versetzt. Dieses wird abgesaugt, mit gesättigter Kochsalzlösung gewaschen, ge trocknet und einige Male mit absol. Äthanol ausgekocht. Die äthanolischen Filtrate werden eingeengt und gekühlt. So erhält man unge- fähr 20 bis 25 g Natriumsalz des 2,4-Dioxy-5- sulfo-phenyl-isobutyl-thioäthers in Form wei sser Blättchen, die sich bei 325 unter Braun färbung zersetzen.
Das Salz löst sich sehr leicht in kaltem Wasser, leicht in wasserhal tigem Methanol, Äthanol und Aceton.
<B> Process for the production of a new aromatic </B> thioether. The present patent relates to a process for the production of a new aromatic thioether, namely 2,4-dioxy-5-sulfo-phenyl-isobutyl-thioether.
This thioether has a strong inhibitory effect on bacterial growth as well as a certain vermicidal effect and is said to be used as a chemotherapeutic.
The process according to the invention for preparing the new aromatic thioether is characterized in that a compound of the formula
EMI0001.0010
a compound of the formula
EMI0001.0011
can act, where X and Y are radicals split off during the reaction, and that the sulfo group is then introduced into the thioether obtained with a sulfurizing agent.
For example, a compound of the formula II in which Y is an halogen atom or another easily split off radical can act on a metal salt of 2,4-dioxy-thiophenol (X = Me, e.g. sodium, potassium, etc.) such as B. is an alkyl or Ai_yl-sulfonyloxy radical. It is furthermore also possible to react 2,4-dioxy-thiophenol with a compound of the formula II in the presence of a basic condensing agent.
The sulfo group can be introduced with the aid of oleum or halosulfonic acids, such as. B. chlorosulfonic acid. , The 2,4-dioxy-5-sulfo-phenyl-isobutyl-thioether obtained in this way forms a sodium salt which crystallizes in white flakes which decompose at 325 with a brown color.
Example: 9.1 g sodium are in 500 cm 3 abs. Dissolved ethanol. 50 g of 2,4-dioxy-thiophenol are added to the solution, and 50 g of isobutyl bromide are added with stirring. It is heated for 3 hours on the steam bath, the ethanol is distilled off, taken up in ether, the ethereal solution is treated with water and then, after drying, it is distilled in vacuo.
The 2,4-dioxy-phenyl-isobutyl-thioether (50 g), boiling below 0.06 mm at <B> 113 </B> to <B> 1150, is dissolved in 300 cubic meters of abs. Dissolved nitrobenzene and treated dropwise with 30 g of chlorosulfonic acid while cooling with ice. Turbine is carried out for 2 hours at 18 to 22, then left to stand overnight, the nitrobenzene solution is shaken out with water and the aqueous solution is concentrated in vacuo to 250 cms.
To clean the solution, after clarifying with animal charcoal, sodium chloride is added to precipitate the sodium salt. This is filtered off with suction, washed with saturated sodium chloride solution, dried and a few times with absol. Boiled ethanol. The ethanolic filtrates are concentrated and cooled. This gives about 20 to 25 g of the sodium salt of 2,4-dioxy-5-sulfo-phenyl-isobutyl-thioether in the form of white flakes which decompose at 325 to turn brown.
The salt dissolves very easily in cold water, easily in water-containing methanol, ethanol and acetone.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH301683T | 1951-11-16 | ||
CH297993T | 1951-11-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH301683A true CH301683A (en) | 1954-09-15 |
Family
ID=25733918
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH301683D CH301683A (en) | 1951-11-16 | 1951-11-16 | Process for the preparation of a new aromatic thioether. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH301683A (en) |
-
1951
- 1951-11-16 CH CH301683D patent/CH301683A/en unknown
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