DE2443256A1 - 3-Phenyl-4,5,6-trichloro-pyridazine derivs prepn - by reacting 3-phenyl-4,5-dihydro-6(1H)-pyridazones with chlorine in phosphorus oxychloride - Google Patents

3-Phenyl-4,5,6-trichloro-pyridazine derivs prepn - by reacting 3-phenyl-4,5-dihydro-6(1H)-pyridazones with chlorine in phosphorus oxychloride

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DE2443256A1
DE2443256A1 DE2443256A DE2443256A DE2443256A1 DE 2443256 A1 DE2443256 A1 DE 2443256A1 DE 2443256 A DE2443256 A DE 2443256A DE 2443256 A DE2443256 A DE 2443256A DE 2443256 A1 DE2443256 A1 DE 2443256A1
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phenyl
chlorine
phosphorus oxychloride
pyridazine
reacting
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Peter Dr Reich-Rohrwig
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Lentia GmbH
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Lentia GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/12—Halogen atoms or nitro radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

3-Phenyl-4,5,6-trichloro-pyridazine derivs. of formula (I): (where R1 and R2 are H or halogen), e.g. 3-phenyl-4,5,6-trichloropyridazine or 3-(p-chlorophenyl)-4,5,6-trichloropyridazine, are prepd. by suspending 3-phenyl-4,5-dihydro-6(5H)-pyridazones of formula (II) in POCl3 and reacting with Cl2. (I) are useful as intermediates for herbicides. Single-stage process giving (I) in good yields and purity. Starting materials (II) are obtainable by cyclising 3-(opt. substd. benzoyl)-propionic acids with hydrazine. The conversion into (I) is effected by passing Cl2 gas through a suspension of (II) in POCl3. The initial reaction temp. is pref. held below 40 degrees C, being increased to up to 100 degrees C during the course of the reaction.

Description

Verfahren zur Heratellung von 3-Phenyl-4, 5, 6-trichlorpyridazinen Die vorliegende Erfindung beinhaltet ein Verfahren zur Herstellung von 3-Phenyl-4,5,6-trichlorpyridazinen aus den entsprechenden 3-Phenyl-pyridazinonen-(6). Process for the preparation of 3-phenyl-4, 5, 6-trichloropyridazines The present invention includes a process for the preparation of 3-phenyl-4,5,6-trichloropyridazines from the corresponding 3-phenyl-pyridazinones- (6).

Es ist aus der österreichischen Patentschrift Nr. 188 332 bekannt, ein Pyridazinderivat, das in Stellung 6 eine Hydroxygruppe enthält, durch Behandeln mit POCl3 oder PCl5 in die entsprechende 6-Chlorverbindung überzuführen.It is known from Austrian patent specification No. 188 332, a pyridazine derivative containing a hydroxyl group at the 6-position by treating to be converted into the corresponding 6-chloro compound with POCl3 or PCl5.

In der Dt-OS 2 031 571 wird ein in 6-Stellung bereits chloriertes Pyridazin mit Chlorierungsmitteln wie Sulfenyle oder Witrosylchlorid weiter chloriert.In German Offenlegungsschrift No. 2,031,571, one is already chlorinated in the 6-position Pyridazine is further chlorinated with chlorinating agents such as sulfenyls or witrosyl chloride.

Weiters sind Pyridazinderivate, die sowohl Chlor- als auch einen Phenylrest tragen, aus der österreichischen Patentschrift Nr. 260 943 und der DT-OS Nr. 2 031 571 bekannt, Jedoch ist dort der Phenylrest am Stickstoff in Stellung 2 gebunden. Auch in der österreichischen Patentschrift Nr. 285 618 sowie in den britischen Patentsohriften Nr. 1 241 527 und 1 248 094 sind chlorhaltige Pyridazinverbindungen genannt.Furthermore, there are pyridazine derivatives that contain both chlorine and a phenyl radical from Austrian Patent No. 260 943 and DT-OS No. 2 031 571, but the phenyl radical is bonded to the nitrogen in position 2 there. Also in the Austrian patent specification No. 285 618 and in the British patent pens No. 1 241 527 and 1 248 094 are mentioned chlorine-containing pyridazine compounds.

Es ist schließlich aus der D?-OS 2 229 745 bekannt, 3-Phenyl-4,5,6-trichlorpyridazin durch Einleiten von Chlor in eine Suspension von 3-Phenylpyridazon-(6) in einem Gemisch von Phosphoroxychlorid und Phosphorpentachlorid darzustellen, wobei die Anwesenheit von Phosphorpentachlorid eine Voraussetzung flir das Gelingen des Verfahrens ist. Dieses ftir die Herstellung von 3-Phenyl-4,5,6-trichlorpyridazin beschriebene Verfahren ist Jedoch umständlich, weil das hiefür notwendige Auagangsprodukt 3-Phenyl-pyridazon-(6) durch Oxydation von 3-Phengl-pyridazinon-(6) mit elementarem Brom in Eisessig gewonnen werden muß. Es benötigt also für die umwandlung von 3-Phenyl-pyridazinon- (6) in 3-Phenyl-4,5,6-trichlorpyridazin zwei getrennte Reaktionsstufen.Finally, it is known from D? -OS 2 229 745, 3-phenyl-4,5,6-trichloropyridazine by introducing chlorine into a suspension of 3-phenylpyridazone- (6) in one Represent a mixture of phosphorus oxychloride and phosphorus pentachloride, the The presence of phosphorus pentachloride is a prerequisite for the success of the process is. This is described for the preparation of 3-phenyl-4,5,6-trichloropyridazine However, the process is cumbersome because the initial product 3-phenyl-pyridazon- (6) obtained by oxidation of 3-Phengl-pyridazinon- (6) with elemental bromine in glacial acetic acid must become. It is therefore required for the conversion of 3-phenyl-pyridazinone- (6) into 3-Phenyl-4,5,6-trichloropyridazine two separate reaction stages.

Es konnte nun gefunden werden, daß man 3-Phenyl-4,5,6-trichlorpyridazine der allgemeinen Formel in der R1 und R2, die gleich oder verschieden sein können, Wasserstoff oder ein Halogenatom bedeuten, auf einfache Weise in einer Reaktionustufe aus 3-Phen'yl-pyridazinonen-(6) der allgemeinen Formel in der R1 und R2 die oben angegebene Bedeutung haben, herstellen kann, indem man diese in Phosphoroxychlorid mit Chlor umsetzt.It has now been found that 3-phenyl-4,5,6-trichloropyridazines of the general formula in which R1 and R2, which can be identical or different, denote hydrogen or a halogen atom, in a simple manner in a reaction stage from 3-phen'yl-pyridazinonen- (6) of the general formula in which R1 and R2 have the meaning given above, can be prepared by reacting them with chlorine in phosphorus oxychloride.

Gegenstand der vorliegenden Erfindung ist demnach ein Verfahren zur Herstellung von 3-Phenyl-4,5,6-trichlorpyridazinen der allgemeinen Formel 1, das dadurch gekennzeichnet ist, daß man 3-Phenyl-pyridazinone-(6) der allgemeinen Formel II in Phosphoroxychlorid suspendiert und mit Chlor umsetzt. Es hat sich als gUnstig erwiesen, zu Beginn die Temperatur des Reaktionsgemisches unter 400 C zu halten, die Temperatur im Laufe der Reaktion aber auf maximal 1000 C zu steigern.The present invention is therefore a method for Preparation of 3-phenyl-4,5,6-trichloropyridazines of the general formula 1, the characterized in that 3-phenyl-pyridazinone- (6) of the general formula II suspended in phosphorus oxychloride and reacted with chlorine. It turned out to be inexpensive proven to keep the temperature of the reaction mixture below 400 C at the beginning, but to increase the temperature to a maximum of 1000 C in the course of the reaction.

Zweckmäßigerweise wird die Umsetzung so ausgeführt, daß man das Pyridazinon bei Raumtemperatur in Phosphorozychlorid suspendiert und Chlor einleitet. Dabei wird die Temperatur durch Kühlen unter 400 C gehalten. Nachdem ca. 1,5 Mol Chlor pro Mol Ausgangsmaterial eingeloitet sind, wird die Temperatur auf 600 bis 900 C gesteigert und die Reaktionen zu Ende geführt.The reaction is expediently carried out in such a way that the pyridazinone suspended in phosphorozychloride at room temperature and introduces chlorine. Included the temperature is kept below 400 ° C. by cooling. After about 1.5 moles of chlorine per mole of starting material are introduced, the temperature is 600 to 900 C. increased and the reactions brought to an end.

Nach Abdampfen des Phosphoroxychlorids wird in Wasser eingerührt, neutralisiert und das Produkt durch Piltration isoliert, getrocknet und gegebenenfalls umkristallisiert. Die Umkristallisation erfolgt zweckmäßig in organischen Lösungamitteln wie Aceton, Tetrachlorkohlenstoff, Methanol usw.After the phosphorus oxychloride has evaporated, it is stirred into water, neutralized and the product isolated by piltration, dried and optionally recrystallized. The recrystallization is expediently carried out in organic solvents such as acetone, carbon tetrachloride, methanol, etc.

Die am Phenylring substituierten 3-Phenyl-pyridazinone-6 werden auf gleiche Weise in die entsprechenden3-Phenyl-4,5,6-trichlorpyridazine übergeführt.The 3-phenyl-pyridazinone-6 substituted on the phenyl ring are on converted in the same way into the corresponding 3-phenyl-4,5,6-trichloropyridazines.

Es ist Uberraschend, daß das erfindungsgemäße Verfahren 3-Phenyl-4,5,6-trichlorpyridazine in guter Ausbeute und Reinheit lisfert, da die hiefür verwendeten Ausgangeverbindungen bei erhöhter Temperatur geringe Stabilität in Phosphoroxychlorid besitzen.It is surprising that the process according to the invention is 3-phenyl-4,5,6-trichloropyridazine in good yield and purity, since the starting compounds used for this have poor stability in phosphorus oxychloride at elevated temperature.

Die für das erfindungsgemäße Verfahren als Ausgangsmaterial benötigten 3-Phenyl-pyridazinone-6 werden in an sich bekannter Weise aus den entsprechenden gegebenenfalls am Phenylkern substituierten 3-Benzoylpropionsäuren durch Cyclisierung mit Hydrazin hergestellt. Es wird hierbei fUr 3-Phenyl-pyridazinon-6 auf die Arbeit von S. Gabriel und J. Colman, Ber, 32/399, für 3-(p-Tolyl)-pyridazinon auf Jene von A.Katzenellenbogen, Ber. 34/3829, fUr 3-(p-Chlorphenyl)-pyridazinon-6 auf Jene von Skraup und Schwammberger, Annalen 462/148 und für 3-(p-Bromphenyl)-pyridazinon-6 und 3-(3,4-Dichlorphenyl)-pyridasinon-6 auf die Veröffentlichung von S.Steck, P.Brundage, L.Pletcher in JACS 75/1117 - 19 verwiesen.The starting material required for the process according to the invention 3-Phenyl-pyridazinone-6 are in a manner known per se from the corresponding 3-benzoylpropionic acids optionally substituted on the phenyl nucleus by cyclization made with hydrazine. It will work here for 3-phenyl-pyridazinon-6 by S. Gabriel and J. Colman, Ber, 32/399, for 3- (p-tolyl) -pyridazinone on those by A.Katzenellenbogen, Ber. 34/3829, for 3- (p-chlorophenyl) -pyridazinon-6 on those von Skraup and Schwammberger, Annalen 462/148 and for 3- (p-bromophenyl) -pyridazinone-6 and 3- (3,4-dichlorophenyl) -pyridasinon-6 based on the publication by S.Steck, P.Brundage, L.Pletcher referenced in JACS 75/1117-19.

3-Phenyl-4,5,6-trichlorpyridazine stellen Zwischenprodukte zur Herstllung von herbizid wirksamen Substanzen dar.3-Phenyl-4,5,6-trichloropyridazines are intermediate products for the production of herbicidally active substances.

In den folgenden Beispielen wird das Verfahren näher erläutert ohne es darauf zu beschränken.In the following examples, the process is explained in more detail without to limit it to that.

Beispiel 1: 174 g (= 1 Mol) 3-Phenylpyridazinon-6 werden in 696 ml Phosphoroxychlorid suspendiert und Chlor mit einer Geschwindigkeit von 1,5 g pro Minute eingeleitet. Die Temperatur wird hiebei zwischen 20 und 300 C gehalten.Example 1: 174 g (= 1 mol) of 3-phenylpyridazinone-6 are in 696 ml Phosphorus oxychloride suspended and chlorine at a rate of 1.5 g per Minute initiated. The temperature is kept between 20 and 300 ° C.

Nach Einleiten von 105 g Chlor wird die Chloreinleitgeschwindigkeit auf 1 g pro Minute reduziert und langsam auf 60 - 700 C aufgewärmt. Die Bildung von 3-Phenyl-4,5,6-trichlorpyridazin ist nach 5 1/2 Stunden beendet.After 105 g of chlorine have been introduced, the rate of introduction of chlorine becomes higher reduced to 1 g per minute and slowly warmed up to 60 - 700 C. The education of 3-phenyl-4,5,6-trichloropyridazine has ended after 5 1/2 hours.

Das Phosphoroxychlorid wird im Vakuum abdestilliert und der zähflüssige Rückstand in 2 1 Wasser eingerührt, mit Ammoniakwasser neutralisiert, filtriert und getrocknet.The phosphorus oxychloride is distilled off in vacuo and the viscous one Stirred residue in 2 l of water, neutralized with ammonia water, filtered and dried.

Ausbeute: 226 g 3-Phenyl-4,5,6-trichlorpyridazin, das entspricht 87 s der Theorie.Yield: 226 g of 3-phenyl-4,5,6-trichloropyridazine, which corresponds to 87 s the theory.

Schmelzpunkt (aus Aceton umkristallisiert) 115 - 1200 C.Melting point (recrystallized from acetone) 115 - 1200 C.

Analyse: C H N cl ber. 46,3 1,94 10,8 41,0 gef. 46,2 t,90 10,9 40,5 Beispiel 2: 62,4 g(= 0,3 Mol) 3-(p-Chlorphenyl)-pyridazinon-6 werden in 300 ml POCl3 suspendiert und unter Kühlen Chlor eingeleitet. Nach einer Stunde wird die Temperatur auf 60 - 750 C erhöht und bei dieser Temperatur weitere 4 Stunden Chlor eingeleitet. lach Stehen über Nacht bei Zimmertemperatur wird auf 2 kg gestoßenes Eis geleert, mit Ammonisklösung neutralisiert und filtriert. Es werden 71 g 3-(p-Chlor-phenyl)-4,5,6-trichlorpyridazin erbalten. Das sind 81 * der Theorie.Analysis: C H N cl calc. 46.3 1.94 10.8 41.0 found. 46.2 t, 90 10.9 40.5 Example 2: 62.4 g (= 0.3 mol) of 3- (p-chlorophenyl) -pyridazinon-6 are dissolved in 300 ml of POCl3 suspended and passed in chlorine with cooling. After an hour the temperature will increased to 60-750 ° C. and chlorine was passed in for a further 4 hours at this temperature. laughing standing overnight at room temperature is emptied onto 2 kg of crushed ice, neutralized with ammonia solution and filtered. There are 71 g of 3- (p-chloro-phenyl) -4,5,6-trichloropyridazine inherited. That's 81 * of the theory.

Sohmelzpunkt (aus Tetrachlorkohlenstoff) 155-157°C Analyse: C H N Cl ber. 40,9 1,4 9,5 48,2 gef. 40,9 1,3 9,6 48,7 Beispiel 3: Es werden 50,6 g (0,2 Mol) 3-(p-Bromphenyl)-pyridazinon-6 in 200 ml Phosphoroxychlorid suspendiert und bei Zimmertemperatur Chlor in einem schwachen Strom eingeleitet. Nach einer Stunde wird auf 600 C erwärmt und weitere 5 Stunden Chlor eingeleitet. Einrühren der Lösung in 250 ml Wasser + 750 g Eis, Neutralisieren mit wäßriger Ammoniaklösung, Filtration und Trocknung ergibt 65 g 3-(p-Bromphenyl)-4,5,6-trichlorpyridazin.Soil melting point (made from carbon tetrachloride) 155-157 ° C Analysis: C H N Cl calc. 40.9 1.4 9.5 48.2 found. 40.9 1.3 9.6 48.7 Example 3: There are 50.6 g (0.2 mol) of 3- (p-bromophenyl) pyridazinone-6 suspended in 200 ml of phosphorus oxychloride and introduced chlorine in a gentle stream at room temperature. After a Hour is heated to 600 C and introduced a further 5 hours of chlorine. Stir in the solution in 250 ml of water + 750 g of ice, neutralize with aqueous ammonia solution, Filtration and drying gives 65 g of 3- (p-bromophenyl) -4,5,6-trichloropyridazine.

Das entspricht 96, 5 % der Theorie.That corresponds to 96.5% of theory.

Schmelzpunkt (aus Tetrachlorkohlenstoff umkristallisiert) 158 - 1610 C Analyse: C H N Cl Br ber. 35,4 1,3 8,3 31,4 23,6 gef. 35,7 1,3 8,0 31,2 22,5 Beispiel 4: 73 g (0,3 Mol) 3-(3,4-Dichlorphenyl)-pyridazinon-6 werden in 250 ml Phosphoroxychlorid suspendiert und wEhrend 10 Stunden Chlor eingeleitet. Die Temperatur steigt zu Beginn langsam an und wird in der Folge zwischen 40 und 650 C gehalten. Man läßt Uber Nacht stehen und filtriert 45 g 3-(3,4-Dichlorphenyl)-4,5,6-trichlorpyridazin (Nadeln) ab. Zersetzung des Phosphoroxychlorids durch Einrühren in Wasser und Eis, Neutralisieren, Filtrieren und Trocknen gibt weitere 44 g Produkt. Das entspricht zusammen einer Ausbeute von 91 % der Theorie.Melting point (recrystallized from carbon tetrachloride) 158 - 1610 C Analysis: C H N Cl Br calc. 35.4 1.3 8.3 31.4 23.6 found. 35.7 1.3 8.0 31.2 22.5 Example 4: 73 g (0.3 mol) of 3- (3,4-dichlorophenyl) pyridazinone-6 are dissolved in 250 ml of phosphorus oxychloride suspended and introduced chlorine for 10 hours. The temperature rises at the beginning slowly and is then kept between 40 and 650 ° C. You leave overnight stand and filtered 45 g of 3- (3,4-dichlorophenyl) -4,5,6-trichloropyridazine (needles) away. Decomposition of the phosphorus oxychloride Stir in water and ice, neutralizing, filtering and drying gives another 44 g of product. That together corresponds to a yield of 91% of theory.

Schmelzpunkt (des aus POC13 kristallisierten Produkts) 176 - 1770 c.Melting point (of the product crystallized from POC13) 176 - 1770 c.

Analyse: C H N Cl ber. 36,6 0,92 8,6 53,9 gef. 36,5 0,9 8,5 53,7Analysis: C H N Cl calcd. 36.6 0.92 8.6 53.9 found. 36.5 0.9 8.5 53.7

Claims (2)

P a t e n t a n s p r ü c h e 1. Verfahren zur Herstellung von 3-Phenyl-4n5,6-trichlorpyridazinen der allgemeinen Formel in der R1 und R2, die gleich oder verschieden sein können, Wasserstoff oder ein Halogen bedeuten, dadurch gekennzeichnet, daß 3-Phenyl-pyrldazinone-(6) der allgemeinen Formel in der R1 und R2 die oben angegebene Bedeutung haben, in Phosphoroxychlorid suspendiert und mit Chlor umgesetzt werden.P atent claims 1. Process for the preparation of 3-phenyl-4n5,6-trichloropyridazines of the general formula in which R1 and R2, which can be identical or different, denote hydrogen or a halogen, characterized in that 3-phenyl-pyrldazinone- (6) of the general formula in which R1 and R2 have the meaning given above, are suspended in phosphorus oxychloride and reacted with chlorine. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß zu Beginn der Reaktion eine Temperatur von unter 40°C eingehalten und die Temperatur im Laufe der Umsetzung auf maximal 100°C erhöht wird.2. The method according to claim 1, characterized in that at the beginning the reaction maintained a temperature of below 40 ° C and the temperature in the course the implementation is increased to a maximum of 100 ° C.
DE2443256A 1974-09-10 1974-09-10 3-Phenyl-4,5,6-trichloro-pyridazine derivs prepn - by reacting 3-phenyl-4,5-dihydro-6(1H)-pyridazones with chlorine in phosphorus oxychloride Pending DE2443256A1 (en)

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