CH275103A - Process for the preparation of a basic ether of an ortho-substituted phenol. - Google Patents
Process for the preparation of a basic ether of an ortho-substituted phenol.Info
- Publication number
- CH275103A CH275103A CH275103DA CH275103A CH 275103 A CH275103 A CH 275103A CH 275103D A CH275103D A CH 275103DA CH 275103 A CH275103 A CH 275103A
- Authority
- CH
- Switzerland
- Prior art keywords
- ortho
- dimethylamino
- preparation
- substituted phenol
- ether
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 6
- 150000002989 phenols Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- -1 alkali metal salt Chemical class 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010992 reflux Methods 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 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical class C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines basischen Äthers eines ortho-substituierten Phenöls. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines basischen Äthers eines ortho-substituierten Phenols. Das Verfahren ist dadurch gekennzeichnet, dass man einen reaktionsfähigen Ester des fl-Di- methylamino-isopropanols mit einer den Rest
EMI0001.0006
einführenden Verbindung, wie z. B. mit 2-(o- Oxy-benzyl)-thiophen oder einem seiner Salze, veräthert.
Die erhaltene neue Verbindung, das 2-[o- (ss -Dimethjamino-isopropoxy) -benzyl]-thio- phen, siedet unter einem Druck von 0,6 mm bei 149 bis 150 . Sie soll therapeutische Ver wendung finden.
<I>Beispiel:</I> Unter gutem Rühren und Erwärmen am Rückflusskühler unter Feuchtigkeitsabschluss wird aus 20 Teilen Methylalkohol und 2,3 Tei len Natrium in 250 Teilen abs. Toluol das Alkoholat dargestellt. Dann werden 19 Teile 2-(o-Oxy-benzyl)-thiophen zugegeben und der Methylalkohol vollständig abdestilliert. Hier auf werden bei etwa 90 bis 95 13 Teile fl- Dimethylamino - isopropylchlorid zugetropft. Nach beendigtem Zutropfen wird noch 3 Std.
unter Rückfluss erhitzt. Nach dem Abkühlen und Versetzen mit etwas Äther wird der basi sche Phenoläther mit total 300 Teilen 2n- Salzsäure in 2 Portionen aufgenommen, mit konz. Natronlauge unter guter Eiskühlung alkalisch gestellt und ausgeäthert. Die ätheri sche Lösung wird mit Natriumsulfat getrock net, abfiltriert, der Äther abdestilliert und der Rückstand der Vakuiundestillation unterwor fen.
Unter 0,6 mm Druck geht das 2-[o-(B- Dimethylamino-isopropoxy)-benzyl] -thiophen bei 149 bis 150 als leicht viskoses Öl über.
Process for the preparation of a basic ether of an ortho-substituted phen oil. The present patent is a process for the preparation of a basic ether of an ortho-substituted phenol. The method is characterized in that a reactive ester of fl-dimethylamino-isopropanol with one of the remainder
EMI0001.0006
introductory compound, such as B. with 2- (o-oxy-benzyl) thiophene or one of its salts, etherified.
The new compound obtained, 2- [o- (ss -dimethjamino-isopropoxy) -benzyl] -thiophene, boils at 149 to 150 under a pressure of 0.6 mm. It should find therapeutic use.
<I> Example: </I> With thorough stirring and heating on the reflux condenser with exclusion of moisture, 20 parts of methyl alcohol and 2.3 parts of sodium in 250 parts of abs. Toluene represented the alcoholate. Then 19 parts of 2- (o-oxy-benzyl) thiophene are added and the methyl alcohol is completely distilled off. Here at about 90 to 95 13 parts of fl-dimethylamino-isopropyl chloride are added dropwise. After the dropping is complete, another 3 hours.
heated under reflux. After cooling and adding a little ether, the basic phenol ether is taken up with a total of 300 parts of 2N hydrochloric acid in 2 portions, with conc. Sodium hydroxide solution made alkaline with good ice cooling and extracted with ether. The ethereal solution is dried with sodium sulfate, filtered off, the ether is distilled off and the residue is subjected to vacuum distillation.
Under 0.6 mm pressure, the 2- [o- (B-dimethylamino-isopropoxy) -benzyl] -thiophene passes over at 149 to 150 as a slightly viscous oil.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH275103T | 1949-01-06 | ||
| CH271776T | 1949-01-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH275103A true CH275103A (en) | 1951-04-30 |
Family
ID=25731324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH275103D CH275103A (en) | 1949-01-06 | 1949-01-06 | Process for the preparation of a basic ether of an ortho-substituted phenol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH275103A (en) |
-
1949
- 1949-01-06 CH CH275103D patent/CH275103A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH275103A (en) | Process for the preparation of a basic ether of an ortho-substituted phenol. | |
| CH275104A (en) | Process for the preparation of a basic ether of an ortho-substituted phenol. | |
| DE582968C (en) | Process for the production of nuclear iodized carvacrol | |
| CH211238A (en) | Process for the preparation of a condensation product which can be used for pest control. | |
| CH311704A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH211237A (en) | Process for the preparation of a condensation product which can be used for pest control. | |
| CH311701A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH193611A (en) | Process for the preparation of a condensation product which can be used for pest control. | |
| CH205770A (en) | Process for the preparation of a condensation product which can be used for pest control. | |
| CH268988A (en) | Process for the production of a dibenzopyran derivative. | |
| CH345645A (en) | Process for the preparation of thiophosphoric acid esters | |
| CH307885A (en) | Process for the preparation of a bactericidal salicylanilide. | |
| CH240376A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240371A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH298785A (en) | Process for the preparation of a diquartar diammonium salt. | |
| CH240398A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH221826A (en) | Process for the production of a new condensation product. | |
| CH311694A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH308271A (en) | Process for the preparation of a new triphenylmethane derivative containing sulfone groups. | |
| CH311688A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH205772A (en) | Process for the preparation of a condensation product which can be used for pest control. | |
| CH311686A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH137144A (en) | Process for the preparation of a basic phenol alkyl ether. | |
| CH311692A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH214776A (en) | Process for the production of a new condensation product. |