CH199044A - Process for the preparation of a p-phenanthroline derivative. - Google Patents
Process for the preparation of a p-phenanthroline derivative.Info
- Publication number
- CH199044A CH199044A CH199044DA CH199044A CH 199044 A CH199044 A CH 199044A CH 199044D A CH199044D A CH 199044DA CH 199044 A CH199044 A CH 199044A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenanthroline
- preparation
- phenanthroline derivative
- boiling
- dimethyl
- Prior art date
Links
- DATYUTWESAKQQM-UHFFFAOYSA-N 4,7-phenanthroline Chemical class C1=CC=C2C3=CC=CN=C3C=CC2=N1 DATYUTWESAKQQM-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines p-Phenanthrolinabkömmlings. Es wurde gefunden, dass man zu einem neuartigen Abkömmling des p-Phenanthro- lins dadurch gelangt, dass man auf 2.2'-Di- methyl-4.4'-dihalogen-p-phenanthrolin (Halo gen in p-Stellung zu den Ringstickstoff atomen) Thioharnstoff einwirken lässt und aus dem zunächst entstandenen Salz die freie Base abscheidet. Die Umsetzung erfolgt zweck- mässig unter Erwärmen in Gegenwart von Löse-. oder Verdünnungsmitteln, zum Beispiel Wasser oder Alkoholen.
Dabei werden unter Abspaltung der beiden Halogenatome die 4- und V-Stellung des p-Phenanthrolins unter Ringbildung durch Schwefel verknüpft zum Beispiel gemäss folgendem Reaktionsschema:
EMI0001.0015
Das so erhältliche 2.2'-Dimethyl-4.4'- thio-p-phenanthrolin bildet weisse Kristalle vom F. 229-2311, Es zeichnet sich durch schmerzstillende Wirkung aus. Es soll thera peutische Verwendung finden.
Beispiel <I>1:</I> 10 g 2. 2'-Dinmethyl-4.4'-dichlor-p-phenan- throlin werden mit 2,8 g Thioharnstoff und 45 ein' Alkohol zum Sieden erhitzt. Nach etwa 20 Minuten langem Kochen tritt unter Hellgelbfärbung derFlüssigkeitvorübergehend zum Teil Lösung ein, worauf sich eine reich liche Menge einer Hellgelben raumfüllenden Masse unter Verfestigung der Reaktionsmi schung und unter starkem Sieden des Alkohols abscheidet. Mai) erhitzt noch eine Stunde zum Sieden, wobei die Masse wieder dünnflüssiger wird.
Nach dein Erkalten wird abgesaugt, das erhaltene Salz in heissen) Wasser gelöst und die heisse Lösung durch Zusatz vor) Ka- liunicarbonatlösung alkaliseh gemacht. Dabei scheidet sich ein weisser kri,talliner Nieder schlag ab, der abgesaugt, gewaschen und aus Alkohol umkristallisiert wird. Das so erhal tene 2.2'-Dimethyl-4.4'-thio-p-plienarithroliri stellt eine weisse, fein kristalline Masse dar, die bei 299-2811 schmilzt.
Auch bei Anwendung eines Überschusses von Thioliarnstoff gelangt man zum gleichen Endprodukt. Beispiel <I>2:</I> 10 g 2. 2'-Dimethyl-4. 4'-dichlor-p-phenan- throlin werden mit 5,6 g Thioharnstoff in 100 cm' Wasser zum Sieden erhitzt. Nach etwa 5-6stündigem Kochen tritt Lösung ein.
Beim Versetzen der heissen Lösung mit Kaliumoarbonat bis zur alkaliscben Reaktion erhält man das bereits im Beispiel 1 beschrie bene 2.2'-Dimethyl-4.4'-thio-p-pherianthrolin.
Process for the preparation of a p-phenanthroline derivative. It has been found that a novel derivative of p-phenanthroline is obtained by using thiourea on 2.2'-dimethyl-4.4'-dihalogeno-p-phenanthroline (halogen in p-position to the ring nitrogen atoms) lets act and separates the free base from the initially formed salt. The reaction is expediently carried out with heating in the presence of solvent. or diluents, for example water or alcohols.
The 4- and V-positions of the p-phenanthroline are linked with formation of rings by sulfur, for example according to the following reaction scheme:
EMI0001.0015
The 2.2'-dimethyl-4.4'-thio-p-phenanthroline that can be obtained in this way forms white crystals of F. 229-2311, it is characterized by its analgesic effect. It should be used therapeutically.
Example <I> 1 </I> 10 g of 2. 2'-Dinmethyl-4.4'-dichloro-p-phenanthroline are heated to boiling with 2.8 g of thiourea and 45% of an alcohol. After about 20 minutes of boiling, the liquid temporarily partially dissolves with a light yellow color, whereupon a large amount of a light yellow, space-filling mass is deposited with solidification of the reaction mixture and with vigorous boiling of the alcohol. Mai) is heated to boiling for another hour, during which the mass becomes thinner again.
After it has cooled down, it is suctioned off, the salt obtained is dissolved in hot water and the hot solution is made alkaline by adding potassium carbonate solution. A white crystalline precipitate separates out, which is suctioned off, washed and recrystallized from alcohol. The 2.2'-dimethyl-4.4'-thio-p-plienarithroliri obtained in this way is a white, finely crystalline mass that melts at 299-2811.
Even if an excess of thiolar is used, the same end product is obtained. Example <I> 2: </I> 10 g of 2. 2'-dimethyl-4. 4'-dichloro-p-phenanthroline are heated to boiling with 5.6 g of thiourea in 100 cm 'of water. After about 5-6 hours of boiling, solution occurs.
When the hot solution is mixed with potassium carbonate until an alkaline reaction occurs, the 2,2'-dimethyl-4,4'-thio-p-pherianthroline already described in Example 1 is obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE199044X | 1936-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199044A true CH199044A (en) | 1938-07-31 |
Family
ID=5757337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199044D CH199044A (en) | 1936-07-08 | 1937-05-29 | Process for the preparation of a p-phenanthroline derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199044A (en) |
-
1937
- 1937-05-29 CH CH199044D patent/CH199044A/en unknown
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