CH298046A - Process for the preparation of a new imidazoline. - Google Patents
Process for the preparation of a new imidazoline.Info
- Publication number
- CH298046A CH298046A CH298046DA CH298046A CH 298046 A CH298046 A CH 298046A CH 298046D A CH298046D A CH 298046DA CH 298046 A CH298046 A CH 298046A
- Authority
- CH
- Switzerland
- Prior art keywords
- imidazoline
- phenyl
- new
- preparation
- ethylenediamine
- Prior art date
Links
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000155 melt Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 150000008043 acidic salts Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000003916 ethylene diamine group Chemical group 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- -1 imide halides Chemical class 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Imidazolins. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines neuen Imidazolins, welches dadurch gekennzeichnet ist, dass man Äthylendiamin mit einer den Rest
EMI0001.0006
abgebenden Verbindung umsetzt..
Als solche können z. B. die N,N-(p-Oxy- pheny 1) - N - phenyl - amino - essigsäure, ihre Imidoäther, Imidhalogenide, Thioimidoäther, Ester, Halogenide, Amide, Thioamide oder Amidine oder ihr Nitril verwendet werden. Das Verfahren kann auch so durchgeführt erden, dass die Ausgangsstoffe unmittelbar nach ihrer Bildung umgesetzt werden, z. B.
das Äthylendiamin unmittelbar nach einer Bildung aus äthylenharnstoff. Setzt man das Nitril direkt mit Äthylendiamin um, so wird die Reaktion vorzugsweise in Gegenwart von Schwefelwasserstoff oder Schwefelwasserstoff bildenden l-Titteln, wie Schwefelkohlenstoff, durchgeführt. Die Umsetzung des Nitrils mit :lthylendiamin kann auch so erfolgen, dass man letzteres in Form seiner Monosalze, wie z. B. seines p-Toluolsulfonates, verwendet..
Die Reaktion lässt sich in An- oder Abwesenheit von Verdünnungs- und/oder Kondensations- witteln bei niederer oder höherer Temperatur imd verschiedenen Drucken vornehmen. Das Verfahren lässt sich auch in zwei Stufen durchführen, indem zuerst das Asylderivat des Äthylendiamins gebildet und dieses mit. Wasser abspaltenden Mitteln, wie Calcium- oxyd oder Phosphorpentoxyd, erhitzt wird.
Das erhaltene 2-[N-(p-Oxy-phenyl)-N-phe- nyl-amino-methyl] -imidazolin ist neu und schmilzt bei 166 bis 170 . Es bildet leicht Salze mit anorganischen oder organischen Säuren, z. B. mit Halogenwasserstoffsäuren, wie der Salzsäure, mit Schwefelsäure-, Phos phorsäure, 1Vlethansulfosäure oder Toluolsulfo- säure, Essigsäure und dergleichen, so z. B. ein salzsaures Salz vom Schmelzpunkt 225 .
Das neue Imidazolin zeigt sympathicoly- tische Wirkung und soll als Heilmittel Ver wendung finden.
Beispiel: 25,50 Teile N-(p-Oxy-phenyl)-N-phenyl- amino-aceto-nitril (erhalten aus N-(p-Oxy- phenyl)-phenyl-amin, Formaldehyd und Ka- liumcyanid in Eisessig) und 19,0 Teile Äthy- lendiamin werden in Gegenwart. von 0,3 Teilen Schwefelwasserstoff 8 Stunden atü dem sie denden Wasserbad erhitzt.
Das Reaktionspro dukt wird in warmem Alkohol gelöst und unter vermindertem Druck eingedampft. zur Entfernung des überschüssigen Äthylendi- amins. Der Rückstand wird nochmals in Al kohol gelöst. und kristallisieren gelassen. Durch Abtrennen der Kristalle erhält man das 2-[N-(p-Oxy-phenyl)-N-phenyl-amino-me- thyl] -imidazolin, das bei 166 bis 170 schmilzt..
Es wird in Alkohol gelöst, mit alkoholischer Salzsäure versetzt, eingeengt und dann zur erhaltenen Lösung Essigester zugegeben, wor- auf das Hydrochlorid der genannten Base, vom Schmelzpunkt 225 , auskristallisiert. Es besitzt die Formel
EMI0002.0003
Process for the preparation of a new imidazoline. The subject of the present patent is a process for the preparation of a new imidazoline, which is characterized in that one ethylenediamine with one of the rest
EMI0001.0006
transferring connection.
As such, e.g. B. the N, N- (p-Oxypheny 1) - N - phenyl - amino - acetic acid, its imido ethers, imide halides, thioimido ethers, esters, halides, amides, thioamides or amidines or their nitrile can be used. The method can also be carried out so that the starting materials are implemented immediately after their formation, e.g. B.
the ethylene diamine immediately after formation from ethylene urea. If the nitrile is reacted directly with ethylenediamine, the reaction is preferably carried out in the presence of hydrogen sulfide or hydrogen sulfide-forming agents, such as carbon disulfide. The reaction of the nitrile with: ethylenediamine can also be carried out in such a way that the latter is in the form of its monosalts, such as. B. its p-toluenesulfonate, used ..
The reaction can be carried out in the presence or absence of dilution and / or condensation media at lower or higher temperatures and at various pressures. The process can also be carried out in two stages, by first forming the asylum derivative of ethylenediamine and this with. Agents that split off water, such as calcium oxide or phosphorus pentoxide, are heated.
The 2- [N- (p-oxy-phenyl) -N-phenyl-aminomethyl] -imidazoline obtained is new and melts at 166 to 170. It easily forms salts with inorganic or organic acids, e.g. B. with hydrohalic acids such as hydrochloric acid, with sulfuric acid, phosphoric acid, 1Vlethanesulfonic acid or toluenesulfonic acid, acetic acid and the like, so z. B. a hydrochloric acid salt with a melting point of 225.
The new imidazoline has a sympathetic effect and is said to be used as a remedy.
Example: 25.50 parts of N- (p-oxy-phenyl) -N-phenyl-amino-aceto-nitrile (obtained from N- (p-oxy-phenyl) -phenyl-amine, formaldehyde and potassium cyanide in glacial acetic acid) and 19.0 parts of ethylenediamine are in the presence. heated by 0.3 parts of hydrogen sulfide for 8 hours atü the water bath.
The reaction product is dissolved in warm alcohol and evaporated under reduced pressure. to remove the excess ethylene diamine. The residue is dissolved again in alcohol. and left to crystallize. Separating the crystals gives 2- [N- (p-oxy-phenyl) -N-phenyl-aminomethyl] -imidazoline, which melts at 166 to 170 ..
It is dissolved in alcohol, mixed with alcoholic hydrochloric acid, concentrated and then ethyl acetate added to the resulting solution, whereupon the hydrochloride of the base mentioned, with a melting point of 225, crystallizes out. It has the formula
EMI0002.0003
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH284620T | 1947-01-31 | ||
| CH298046T | 1947-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH298046A true CH298046A (en) | 1954-04-15 |
Family
ID=25732447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH298046D CH298046A (en) | 1947-01-31 | 1947-01-31 | Process for the preparation of a new imidazoline. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH298046A (en) |
-
1947
- 1947-01-31 CH CH298046D patent/CH298046A/en unknown
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