CH184494A - Process for the preparation of a polymethine compound substituted on the central carbon atom of the polymethine chain. - Google Patents
Process for the preparation of a polymethine compound substituted on the central carbon atom of the polymethine chain.Info
- Publication number
- CH184494A CH184494A CH184494DA CH184494A CH 184494 A CH184494 A CH 184494A CH 184494D A CH184494D A CH 184494DA CH 184494 A CH184494 A CH 184494A
- Authority
- CH
- Switzerland
- Prior art keywords
- polymethine
- substituted
- represent
- process according
- acid amide
- Prior art date
Links
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Verfahren zur Herstellung einer am mittelständigen Kohlenstoffatom der Polymethinkette substituierten Polymethinverbindung. Es ist bereits bekannt, Polymethinver- bindungen, die am mittelständigen Kohlen stoffatom der Polymethingruppe substituiert sind, herzustellen, indem man Orthocarbon- säureester mit quartären Ammoniumsalzen stickstoffhaltiger heterozyklischer Basen kon densiert.
Die Herstellung der für das Ver fahren notwendigen Orthoester ist zum Teil sehr umständlich, zum Teil ist eine grosse Anzahl von Orthoestern bisher noch nicht be kannt und ihre Herstellung nach den üb lichen Methoden nicht möglich.
Gegenstand der Erfindung ist ein Ver fahren zur Herstellung einer am mittelstän digen Kohlenstoffatom der Polymethinkette substituierten Polymethinverbindung, bei dem man 2-Methylbenzthiazol-jodäthylat mit einer Verbindung der allgemeinen Formel
EMI0001.0022
umsetzt, worin Rn, R2 organische einwertige Gruppen, zum Beispiel Alkyl-, Aralkyl-,
Aryl- oder substituierte Arylgruppen dar stellen und die beiden unbezeielhneten Striche mit Sauerstoff verbunden sind. Das ent stehende 1,1'-Diäthyl-mesopropyl-benzthio- carbocyaninjoditl bildet dunkelgrüne. Kri stalle.
Die Umsetzung kann gegebenenfalls in Gegenwart von Lösungs- oder Kondensa tionsmitteln erfolgen. Besonders geeignet zur Kondensation ist das substituierte Säure- amid von der Formel
EMI0001.0038
das durch .Spaltung des in a-Stellung zum Stickstoff durch n-Propyl substituierten ent sprechenden Oxazols erhalten werden kann. Besonders reaktionsfähig ist das bei einer Spaltung eines solchen Oxazols mittels Alkalialkylaten auftretende substituierte
Säureamid mit acetalisierter Carbonylgruppe, aus welchem durch Einwirkung von Säure das eigentliche substituierte Säureamid er halten werden kann.
Das nach dem vorliegenden Verfahren hergestellte 1,1'-Diäthyl - mesopropyl - benz- thiocarbocyaninjodid hat die Formel
EMI0002.0013
<I>Beispiel:</I> 16 g 2=n-Propylbenzoxazol werden mit 12 eins Dimethylsulfat auf dem Wasserbad erhitzt.
Das gebildete 2-Propylbenzoxazol- dimethylsulfat wird durch Erwärmung mit Natriumäthylatlösung zu dem entsprechen den substituierten Buttersäureamid mit acetalisierter Carbonylgruppe gespalten. Zu der alkoholischen Lösung des acetalisierten Buttersäureamids werden 6 g 2-Methylbenz- thiazoljodäthylat hinzugesetzt und die Lö sung etwa 30 bis 60 Minuten gekocht.
Nach dem Erkalten kristallisiert der Farbstoff in dunkelgrün schillernden Kristallen aus.
Process for the preparation of a polymethine compound substituted on the central carbon atom of the polymethine chain. It is already known that polymethine compounds which are substituted on the central carbon atom of the polymethine group can be prepared by condensing orthocarboxylic esters with quaternary ammonium salts of nitrogen-containing heterocyclic bases.
The production of the orthoesters necessary for the process is sometimes very laborious, and in some cases a large number of orthoesters are not yet known and their production by the usual methods is not possible.
The invention relates to a process for the production of a polymethine compound substituted on the middle carbon atom of the polymethine chain, in which 2-methylbenzthiazole iodoethylate is used with a compound of the general formula
EMI0001.0022
converts, in which Rn, R2 organic monovalent groups, for example alkyl, aralkyl,
Aryl or substituted aryl groups represent and the two unmarked lines are connected to oxygen. The resulting 1,1'-diethyl-mesopropyl-benzthio-carbocyaninjoditl forms dark green. Crystals.
The reaction can optionally be carried out in the presence of solvents or condensation agents. The substituted acid amide of the formula is particularly suitable for condensation
EMI0001.0038
which can be obtained by cleavage of the corresponding oxazole substituted by n-propyl in the a-position to the nitrogen. The substituted one which occurs when such an oxazole is cleaved by means of alkali metal alkylates is particularly reactive
Acid amide with acetalized carbonyl group, from which the actual substituted acid amide can be obtained by the action of acid.
The 1,1'-diethyl - mesopropyl - benzthiocarbocyanine iodide produced by the present process has the formula
EMI0002.0013
<I> Example: </I> 16 g of 2 = n-propylbenzoxazole are heated with 12 units of dimethyl sulfate on a water bath.
The 2-propylbenzoxazole dimethyl sulfate formed is cleaved by heating with sodium ethylate solution to give the substituted butyric acid amide with acetalized carbonyl group. 6 g of 2-methylbenzethiazole iodine ethylate are added to the alcoholic solution of the acetalized butyric acid amide and the solution is boiled for about 30 to 60 minutes.
After cooling, the dye crystallizes in shimmering dark green crystals.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE184494X | 1933-06-10 | ||
| CH181813T | 1934-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH184494A true CH184494A (en) | 1936-05-31 |
Family
ID=25720606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH184494D CH184494A (en) | 1933-06-10 | 1934-06-08 | Process for the preparation of a polymethine compound substituted on the central carbon atom of the polymethine chain. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH184494A (en) |
-
1934
- 1934-06-08 CH CH184494D patent/CH184494A/en unknown
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