CH301701A - Process for the preparation of a new aromatic thioether. - Google Patents
Process for the preparation of a new aromatic thioether.Info
- Publication number
- CH301701A CH301701A CH301701DA CH301701A CH 301701 A CH301701 A CH 301701A CH 301701D A CH301701D A CH 301701DA CH 301701 A CH301701 A CH 301701A
- Authority
- CH
- Switzerland
- Prior art keywords
- thioether
- compound
- formula
- preparation
- new aromatic
- Prior art date
Links
- -1 aromatic thioether Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000000973 chemotherapeutic effect Effects 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung eines neuen aromatischen Thioäthers. Das vorliegende Patent bezieht sich auf ein Verfahren zur Herstellung eines neuen aroma tischen Thioäthers, nämlich des 2-Oxy-4-amino- pheny l-n-butyl-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 CI3-0H2-CH2-CH2 Y il einwirken lässt, wobei X und Y sich bei der Reaktion abspaltende Reste bedeuten.
Man kann beispielsweise auf ein Metallsalz des 2-Oxy-4-amino-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 ab spaltenden Rest, wie z. B. einen Alkyl- oder Aryl-sulfonyloxyrest, bedeutet.
Es ist weiter auch möglich, das 2-Oxy-4- amino-thiophenol in Gegenwart eines basischen Kondensationsmittels mit einer Verbindung der Formel II umzusetzen. Der auf diese Weise erhaltene 2-Oxy-4- amino-phenyl-n-butyl-thioäther bildet farb lose Kristalle, die bei 91 schmelzen.
<I>Beispiel:</I> 3,6g Natrium werden in 300 ems abs. Äthanol gelöst. Die Lösung wird mit 22 g 2-Oxy-4-amino-thiophenol versetzt und unter Rühren 32 g n-Butylbromid zugefügt. Man kocht 31/2 Stunden auf dem Dampfbad und verdampft dann zur Trockne. Der Rückstand wird in Äther aufgenommen und die ätheri sche Lösung mit Wasser gewaschen. Nach dem Trocknen der Ätherlösung wird wieder verdampft und der Rückstand einige Male mit Petroläther ausgekocht und diese Eluate ver dampft. Durch Umkristallisieren des Rück .
'standes aus Ligroin gewinnt man den bei 91 schmelzenden 2-Oxy-4-amino-phenyl-n-butyl- thioäther in Form von farblosen Blättchen.
Die neue Verbindung löst. sich leicht in Äthanol, Äther, Chloroform, Aceton, Essig- ester,-Benzol und heissem Ligroin, wenig in kaltem Ligroin und ist praktisch unlöslich in Wasser.
Process for the preparation of a new aromatic thioether. The present patent relates to a process for the preparation of a new aromatic thioether, namely the 2-oxy-4-aminopheny l-n-butyl 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 CI3-0H2-CH2-CH2 Y il can act, where X and Y are radicals split off during the reaction.
For example, a metal salt of 2-oxy-4-aminothiophenol (X = Me, e.g. sodium, potassium, etc.) can be treated with a compound of the formula II in which Y is a halogen atom or another easily cleaving remainder, such as B. is an alkyl or aryl sulfonyloxy radical.
It is also possible to react the 2-oxy-4-aminothiophenol with a compound of the formula II in the presence of a basic condensing agent. The 2-oxy-4-aminophenyl-n-butyl-thioether obtained in this way forms colorless crystals which melt at 91.
<I> Example: </I> 3.6g sodium are in 300 ems abs. Dissolved ethanol. 22 g of 2-oxy-4-aminothiophenol are added to the solution and 32 g of n-butyl bromide are added with stirring. Cook for 31/2 hours on the steam bath and then evaporate to dryness. The residue is taken up in ether and the ethereal solution is washed with water. After the ether solution has dried, it is evaporated again and the residue is boiled a few times with petroleum ether and these eluates are evaporated. By recrystallizing the back.
The 2-oxy-4-aminophenyl-n-butylthioether, which melts at 91, is obtained from ligroin in the form of colorless flakes.
The new connection loosens. easily in ethanol, ether, chloroform, acetone, ethyl acetate, benzene, and hot ligroin, little in cold ligroin, and is practically insoluble in water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH297993T | 1951-11-16 | ||
| CH301701T | 1951-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH301701A true CH301701A (en) | 1954-09-15 |
Family
ID=25733936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH301701D CH301701A (en) | 1951-11-16 | 1951-11-16 | Process for the preparation of a new aromatic thioether. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH301701A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5478359A (en) * | 1991-06-13 | 1995-12-26 | L'oreal | Process for dyeing keratinous fibers and compositions containing sulfur-containing meta-aminophenses |
-
1951
- 1951-11-16 CH CH301701D patent/CH301701A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5478359A (en) * | 1991-06-13 | 1995-12-26 | L'oreal | Process for dyeing keratinous fibers and compositions containing sulfur-containing meta-aminophenses |
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