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
- -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 2
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 3
- 239000012230 colorless oil Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 claims 1
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001035 drying Methods 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
- 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
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
- 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH301687A (en) | Process for the preparation of a new aromatic thioether. | |
| CH301688A (en) | Process for the preparation of a new aromatic thioether. | |
| CH301692A (en) | Process for the preparation of a new aromatic thioether. | |
| CH301691A (en) | Process for the preparation of a new aromatic thioether. | |
| CH301689A (en) | Process for the preparation of a new aromatic thioether. | |
| DE558647C (en) | Process for the production of basic ethers of aromatic ketones | |
| DE924450C (en) | Process for the preparation of coumarin derivatives | |
| DE932373C (en) | Process for the preparation of coumarin derivatives | |
| CH301684A (en) | Process for the preparation of a new aromatic thioester. | |
| AT205983B (en) | Process for the production of new methylene bis (thionothiolphosphoric acid esters) | |
| DE699772C (en) | Process for the preparation of ª ‰ -oxyaethylcarbaminobenzene-p-arsic acid | |
| DE831692C (en) | Process for the production of a new isothiocyanate | |
| CH301695A (en) | Process for the preparation of a new aromatic thioether. | |
| DE223305C (en) | ||
| DE1026323B (en) | Process for the preparation of insecticidally active O, O-dialkyl-S-phenyl-thionothiolphosphoric acid esters | |
| CH301701A (en) | Process for the preparation of a new aromatic thioether. | |
| AT159725B (en) | Process for the production of nitrogen-containing condensation products. | |
| DE972261C (en) | Process for the preparation of dioxopyrazolidine compounds | |
| CH301697A (en) | Process for the preparation of a new aromatic thioether. | |
| DE1146883B (en) | Process for the preparation of dithiophosphinic acid esters | |
| CH301696A (en) | Process for the preparation of a new aromatic thioether. | |
| CH301698A (en) | Process for the preparation of a new aromatic thioether. | |
| CH311693A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH301694A (en) | Process for the preparation of a new aromatic thioether. | |
| CH311694A (en) | Process for the production of a new basic substituted fatty acid amide. |