CH301687A - Process for the preparation of a new aromatic thioether. - Google Patents
Process for the preparation of a new aromatic thioether.Info
- Publication number
- CH301687A CH301687A CH301687DA CH301687A CH 301687 A CH301687 A CH 301687A CH 301687D A CH301687D A CH 301687DA CH 301687 A CH301687 A CH 301687A
- Authority
- CH
- Switzerland
- Prior art keywords
- thioether
- compound
- formula
- preparation
- amyl
- Prior art date
Links
Classifications
-
- 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
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Verfahren</B> zur Herstellung eines <B>neuen</B> aromatischen Thioäthers. Das vorliegende Patent bezieht sich auf ein Verfahren zur Herstellung eines neuen aromatischen Thioäthers, nämlich des 2,4- Dioxy-phenyl-i-amyl-thioäthers.
Dieser Thioäther hat eine starke Hemm wirkung auf das Bakterienwachstum sowie eine gewisse vermicide Wirkung und soll als Chemotherapeu.ticum Verwendung finden.
Das erfindungsgemässe Verfahren zur Her stellung des neuen aromatischen Thioäthers ist dadurch gekennzeichnet, dass man auf eine Verbindung der Formel
EMI0001.0015
eine Verbindung der Formel
EMI0001.0016
einwirken lässt, wobei X und Y sich bei der Reaktion abspaltende Reste bedeuten.
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 Halogenatom oder einen andern sich leicht abspaltenden Rest, wie z. B. einen Alkyl- oder Aryl-sulfonyloxyrest, bedeutet.
Es ist weiter auch möglich, das 2,4-Dioxy- thiophenol in Gegenwart eines basischen Kon- densationsmittels mit einer Verbindung der Formel II umzusetzen.
Der auf diese Weise erhaltene 2,4-Dioxy- phenyl-i-amyl-thioäther bildet ein unter 0,01 mm bei 120 bis 122 siedendes, farbloses Öl.
<I>Beispiel:</I> 25,0 g 2,4-Dioxy-thiophenol werden in einer Lösung von 4,05 g Natrium in 250 cm3 Äthanol mit 27,1 g iso-Amylbromid 3 Stun den auf dem Wasserbad erhitzt. Darauf de stilliert man den Alkohol ab, nimmt in Äther auf und schüttelt gut mit Wasser durch. Nach dem Trocknen wird der Äther abdestilliert und der Rückstand im Vakuum fraktioniert.
Man erhält so 30,0 g (das sind 80,5 % der Theorie) des unter 0,01 mm bei 120 bis 122 siedenden 2,4-Dioxy-phenyl-i-amyl-thioäthers.
Farbloses Öl; unlöslich in Wasser, verdünn ter Salzsäure und Petroläther; gut löslich in verdünnter Natronlauge; mischbar mit Äthanol, Aceton, Dioxan, Essigester, Äther, Chloroform und Benzol.
<B> Process </B> for the production of a <B> new </B> aromatic thioether. The present patent relates to a process for the preparation of a new aromatic thioether, namely 2,4-dioxy-phenyl-i-amyl-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 chemotherapeu.ticum.
The process according to the invention for preparing the new aromatic thioether is characterized in that a compound of the formula
EMI0001.0015
a compound of the formula
EMI0001.0016
can act, where X and Y are radicals splitting off during the reaction.
For example, a compound of formula II in which Y is a 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 aryl sulfonyloxy radical.
It is also possible to react the 2,4-dioxythiophenol with a compound of the formula II in the presence of a basic condensation agent.
The 2,4-dioxyphenyl-i-amyl-thioether obtained in this way forms a colorless oil boiling below 0.01 mm at 120 to 122 mm.
<I> Example: </I> 25.0 g of 2,4-dioxy-thiophenol are heated in a solution of 4.05 g of sodium in 250 cm3 of ethanol with 27.1 g of iso-amyl bromide for 3 hours on a water bath. The alcohol is then distilled, absorbed in ether and shaken well with water. After drying, the ether is distilled off and the residue is fractionated in vacuo.
30.0 g (that is 80.5% of theory) of the 2,4-dioxy-phenyl-i-amyl thioether boiling below 0.01 mm at 120 to 122 are obtained in this way.
Colorless oil; insoluble in water, dilute hydrochloric acid and petroleum ether; readily soluble in dilute sodium hydroxide solution; miscible with ethanol, acetone, dioxane, ethyl acetate, ether, chloroform and benzene.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH301687T | 1951-08-07 | ||
CH297993T | 1951-11-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH301687A true CH301687A (en) | 1954-09-15 |
Family
ID=25733922
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH301687D CH301687A (en) | 1951-08-07 | 1951-08-07 | Process for the preparation of a new aromatic thioether. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH301687A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5013756A (en) * | 1985-09-26 | 1991-05-07 | Societe De Conseils De Recherches Et D'application Scientifiques (S.C.R.A.S) | Catechol derivatives, a process of preparation thereof, and therapeutical compositions containing the same |
-
1951
- 1951-08-07 CH CH301687D patent/CH301687A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5013756A (en) * | 1985-09-26 | 1991-05-07 | Societe De Conseils De Recherches Et D'application Scientifiques (S.C.R.A.S) | Catechol derivatives, a process of preparation thereof, and therapeutical compositions containing the same |
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