DD279480A1 - PROCESS FOR PREPARING 5,5'-DISUBSTITUTED 2,2'-BIS- (1,3,4-THIADIAZOLES) - Google Patents

PROCESS FOR PREPARING 5,5'-DISUBSTITUTED 2,2'-BIS- (1,3,4-THIADIAZOLES) Download PDF

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Publication number
DD279480A1
DD279480A1 DD32508189A DD32508189A DD279480A1 DD 279480 A1 DD279480 A1 DD 279480A1 DD 32508189 A DD32508189 A DD 32508189A DD 32508189 A DD32508189 A DD 32508189A DD 279480 A1 DD279480 A1 DD 279480A1
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DD
German Democratic Republic
Prior art keywords
bis
thiadiazoles
formula
disubstituted
oxalyl chloride
Prior art date
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DD32508189A
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German (de)
Inventor
Wilfried Thiel
Ernst-Adolf Jauer
Victor Werndl
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Bitterfeld Chemie
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Publication date
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Priority to DD32508189A priority Critical patent/DD279480A1/en
Publication of DD279480A1 publication Critical patent/DD279480A1/en

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  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Die Erfindung beinhaltet ein Verfahren zur Herstellung von neuen 5,5-disubstituierten 2,2-Bis-(1,3,4-thiadiazolen), die als potentielle Absorber fuer den nahen UV-Bereich von Interesse sind. Ausgehend von Arylthiohydraziden und Oxalylchlorid liefert das Verfahren die genannten Verbindungen in einem Reaktionsschritt.The invention includes a process for the preparation of novel 5,5-disubstituted 2,2-bis (1,3,4-thiadiazoles) which are of interest as potential absorbers for the near UV region. Starting from aryl thiohydrazides and oxalyl chloride, the process provides the compounds mentioned in one reaction step.

Description

Beispiel 3Example 3

2,2'-Bis-[5-(2-methylthio-1,3,4-thiadiuzol-5-yl)-1,3,4-thiadiazol] Aus 1,0g 2-Methylthio-1,3,4-thiadiazol-5-thiocarbonsäurehydrazid erhält man dnalog Beispiel 1 0,7g (65%) schwach grünlich gelbes Pulver, F. 319 bis 3210C nach Umkristallisieren aus DMF.2,2'-Bis- [5- (2-methylthio-1,3,4-thiadiol-5-yl) -1,3,4-thiadiazole] From 1.0 g of 2-methylthio-1,3,4- thiadiazole-5-thiocarbonsäurehydrazid obtained dnalog Example 1 0.7 g (65%) pale greenish yellow powder, mp 319 to 321 0 C after recrystallization from DMF.

Beispiel 4Example 4

2,2'-Bis-(5-p-nitrophenyl-1,3,4-thiadiazol) Aus 1,0g p-Nitrothiobenzoesäurehydrazid und 0,32g Oxalylchlorid erhält man analog Beispiel 1 0,6g gelbliches Pulver, F. >2,2'-bis- (5-p-nitrophenyl-1,3,4-thiadiazole) From 1.0 g of p-Nitrothiobenzoesäurehydrazid and 0.32 g of oxalyl chloride obtained analogously to Example 1 0.6 g of yellowish powder, mp>

Claims (2)

Verfahren zur Herstellung von 5,5'-disubstituierten 2,2'-Bis-(1,3,4-thiadiazolen) der Formel (D, in der fl ein aromatischer oder heterocyclischer Rest ist, gekennzeichnet dadurch, daß Thiohydrazide der Formel R-CS-NHNH2 (II), in der R die vorgenannte Bedeutung hat, mit Oxalylchlorid cyclisiert werden. Anwendungsgebiet der Erfindung Die Erfindung betrifft ein Verfahren zur Herstellung von 2,2'-Bis-(1,3,4-thiadiazolen), die in 5,5'-Stellung durch heterocyclische oder aromatische Reste substituiert sind und als potentielle UV-Absorber für den nahen UV-Bereich interessant sind. Charakteristik des bekannten Standes der Technik Die Methoden zur Synthese von 1,3,4-Thiadiazolen sind in „The Chemistry of Heterocyclic Compounds" Vol.4 (1852), S.81 ff. (Editor A. Weißberger) zusammengefaßt. Aus der Reihe der 2,2'-Bis-(1,3,4-thiadiazole) sind bisher nur Dialkylverbindungen beschrieben. Diese wurden durch Kondensation von Diacyloxalhydroziden mit P4S,0 hergestellt. Ziel der Erfindung Ziel der Erfindung ist ein Verfahren, daß die Herstellung von in 5,5'-Stellung durch Aryl- oder Heteroreste substituierten 2,2'-Bis-(1,3,4-thiadiazolen) ermöglicht. Darlegung des Wesens der Erfindung Der Erfindung liegt die Aufgabe zugrunde, 5,5'-disubstituierte 2,2'-Bis-(1,3,4-thiadiazole) in einem Schritt durch zweifache Cyclisierung herzustellen. Erfindungsgemäß werden die Verbindungen der Formel N^/V in db-r R ein Arylrest üder ein heterocyclischer Rest ist, durch Umsetzung von Arylthiohydraziden der Formel R-CS-NHNH2 II, worin R die oben genannte Bedeutung hat, mit Oxalylchlorid erhalten. Ausführungsbeispiele Beispiel 1 2,2'-Bis-[5-(chinazolin-4-on-2-yl)-1,3,4-thiadiazol]A process for preparing 5,5'-disubstituted 2,2'-bis (1,3,4-thiadiazoles) of the formula (D in which fl is an aromatic or heterocyclic radical, characterized in that thiohydrazides of the formula R- The invention relates to a process for the preparation of 2,2'-bis- (1,3,4-thiadiazoles), which are described in. In which R has the abovementioned meaning, is cyclized with oxalyl chloride 5,5'-position are substituted by heterocyclic or aromatic radicals and are interesting as potential ultraviolet absorbers for the near UV region .. DESCRIPTION OF THE PRIOR ART The methods for the synthesis of 1,3,4-thiadiazoles are described in "The Chemistry of Heterocyclic Compounds "Vol.4 (1852), p.81 ff. (Editor A. Weissberger) .This number of 2,2'-bis- (1,3,4-thiadiazoles) so far only dialkyl compounds are described These were prepared by condensation of diacyloxalic hydrocides with P4S, O. Aim of the invention Aim of The invention is a process that enables the preparation of 5,5'-position substituted by aryl or hetero radicals 2,2'-bis (1,3,4-thiadiazoles). DESCRIPTION OF THE INVENTION It is the object of the invention to prepare 5,5'-disubstituted 2,2'-bis- (1,3,4-thiadiazoles) in one step by double cyclization. According to the invention, the compounds of the formula N 1 / V in db-r R is an aryl radical or a heterocyclic radical, by reacting arylthiohydrazides of the formula R-CS-NHNH 2 II, where R has the abovementioned meaning, with oxalyl chloride. EXAMPLES Example 1 2,2'-Bis [5- (quinazolin-4-on-2-yl) -1,3,4-thiadiazole] 1,1 g Chinazolin-4-on-2-thiocarbonsäurehydrazid in 30ml trockenem Toluen v/erden mit einer Lösung von 0,32 g Oxalylchlorid in 10ml Toluen versetzt und erhitzt. Nach 1 Std. fügt man etwa 30ml Dimethylformamid (DMF) zu, kocht das Toluen ab, gibt 3 Tropfen Salzsäure zu und erhitzt 1 Std. am Rückfluß. Das Produkt wird nach dem Erkalten abgesaugt und aus DMF umkristallisiert bzw. mit Dimethylformamid ausgekocht. Man erhält 0,6g (52%) gelbliche Substanz, F. >360°C.1.1 g of quinazolin-4-one-2-thiocarboxylic acid hydrazide in 30 ml of dry toluene are mixed with a solution of 0.32 g of oxalyl chloride in 10 ml of toluene and heated. After 1 h, about 30 ml of dimethylformamide (DMF) are added, the toluene is boiled off, 3 drops of hydrochloric acid are added and the mixture is refluxed for 1 h. The product is filtered off with suction after cooling and recrystallized from DMF or boiled with dimethylformamide. This gives 0.6 g (52%) of a yellowish substance, mp> 360 ° C. Beispiel 2Example 2 2,2'-Bis-[5-(benzimidazol-2-yl)-1,3,4-thiadiazol|2,2'-bis [5- (benzimidazol-2-yl) -1,3,4-thiadiazol | Analog Beispiel 1 erhält man aus 0,96g Benzimidazol-2-thiocarbonsäurehydrazidO,6g (60%) braunes Pulver, F. >360'C.Analogously to Example 1, from 0.96 g of benzimidazole-2-thiocarboxylic acid hydrazide O, 6 g (60%) of brown powder, mp> 360 ° C.
DD32508189A 1989-01-17 1989-01-17 PROCESS FOR PREPARING 5,5'-DISUBSTITUTED 2,2'-BIS- (1,3,4-THIADIAZOLES) DD279480A1 (en)

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DD32508189A DD279480A1 (en) 1989-01-17 1989-01-17 PROCESS FOR PREPARING 5,5'-DISUBSTITUTED 2,2'-BIS- (1,3,4-THIADIAZOLES)

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Application Number Priority Date Filing Date Title
DD32508189A DD279480A1 (en) 1989-01-17 1989-01-17 PROCESS FOR PREPARING 5,5'-DISUBSTITUTED 2,2'-BIS- (1,3,4-THIADIAZOLES)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0843995A2 (en) * 1996-11-20 1998-05-27 Haarmann & Reimer Gmbh Use of substituted benzazoles as UV absorbents, new benzazoles and their preparation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0843995A2 (en) * 1996-11-20 1998-05-27 Haarmann & Reimer Gmbh Use of substituted benzazoles as UV absorbents, new benzazoles and their preparation
EP0843995A3 (en) * 1996-11-20 1999-06-09 Haarmann & Reimer Gmbh Use of substituted benzazoles as UV absorbents, new benzazoles and their preparation

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