CH301691A - Process for the preparation of a new aromatic thioether. - Google Patents
Process for the preparation of a new aromatic thioether.Info
- Publication number
- CH301691A CH301691A CH301691DA CH301691A CH 301691 A CH301691 A CH 301691A CH 301691D A CH301691D A CH 301691DA CH 301691 A CH301691 A CH 301691A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- thioether
- formula
- preparation
- new aromatic
- 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
-
- 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
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen aromatischen Thioäthers. Das vorliegende Patent bezieht sich auf ein Verfahren zur Herstellung eines neuen aro- matisehen Thioäthers, nämlich des 2,4-Dioxy- plienyl-i-butyl-thioäthers.
Dieser Thioäther hat eine starke Hemmwir kung auf das Bakterienwachstum sowie eine @Olewisse v ermicide Wirkung und soll als Chemo- iherapeuticum Verwendung finden.
Das erfindungsgemässe Verfahren zur Her- tellung des neuen aromatischen Thioäthers ist dadurch gekennzeichnet, dass man auf eine Verbindung der Formel
EMI0001.0016
eine Verbindung der Formel
EMI0001.0017
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-srtlfonyloxyrest, 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-butyl-thioäther bildet ein unter 0;06 mm bei 113 bis 115 siedendes, farbloses öl.
Beispiel: 20,0 g 2,4-Dioxy-thiophenol werden in einer Lösung von 3,23 g Natrium in 200 cm3 Äthanol mit 20,0 g iso-Butylbromid 3 Stunden auf dem Wasserbad erhitzt. Darauf destilliert 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 22,0 g (das sind 78,9 % der Theorie) des unter 0,06 mm bei 113 bis 115 siedenden 2,4-Dioxy-phenyl-i-butyl-thioäthers. Farbloses Öl, unlöslich in Wasser, verdünnter Salzsäure und Petroläther; gut löslich in ver dünnter Natronlauge; mischbar mit Äthanol, Aceton, Dioxan, Essigester, Äther, Chloroform und Benzol.
Process for the preparation of a new aromatic thioether. The present patent relates to a process for the production of a new aromatic thioether, namely 2,4-dioxyplienyl-i-butyl-thioether.
This thioether has a strong inhibitory effect on bacterial growth and an @Olewisse v ermicide effect and is said to be used as a chemotherapeutic agent.
The process according to the invention for the production of the new aromatic thioether is characterized in that one refers to a compound of the formula
EMI0001.0016
a compound of the formula
EMI0001.0017
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. an alkyl or aryl-srtlfonyloxyest means. It is also possible to react the 2,4-dioxythiophenol in the presence of a basic condensation agent with a compound of the formula II.
The 2,4-dioxyphenyl-i-butyl-thioether obtained in this way forms a colorless oil boiling below 0.06 mm at 113 to 115.
Example: 20.0 g of 2,4-dioxy-thiophenol are heated in a solution of 3.23 g of sodium in 200 cm3 of ethanol with 20.0 g of isobutyl bromide on a water bath for 3 hours. The alcohol is then distilled off, absorbed in ether and shaken well with water. After drying, the ether is distilled off and the residue is fractionated in vacuo.
This gives 22.0 g (that is 78.9% of theory) of 2,4-dioxy-phenyl-i-butyl-thioether which boils below 0.06 mm at 113 to 115. Colorless oil, insoluble in water, dilute hydrochloric acid and petroleum ether; easily 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 |
---|---|---|---|
CH301691T | 1951-08-07 | ||
CH297993T | 1951-11-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH301691A true CH301691A (en) | 1954-09-15 |
Family
ID=25733926
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH301691D CH301691A (en) | 1951-08-07 | 1951-08-07 | Process for the preparation of a new aromatic thioether. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH301691A (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 CH301691D patent/CH301691A/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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