CS196105B1 - Process for preparing 2-phenyl-4,5-dichlorpyridazin-3-one - Google Patents
Process for preparing 2-phenyl-4,5-dichlorpyridazin-3-one Download PDFInfo
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- CS196105B1 CS196105B1 CS189078A CS189078A CS196105B1 CS 196105 B1 CS196105 B1 CS 196105B1 CS 189078 A CS189078 A CS 189078A CS 189078 A CS189078 A CS 189078A CS 196105 B1 CS196105 B1 CS 196105B1
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- phenyl
- amino
- dichloropyridazin
- chloropyridazin
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- Pyridine Compounds (AREA)
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Description
Predmetom vynálezu je sposob výroby 2-fenyl-4,5-díchlórpyridazín-3-ónu.The present invention provides a process for the preparation of 2-phenyl-4,5-dichloropyridazin-3-one.
2-fenyl-4,5-dichlórpyridazón je východiskovým produktom pri výrobě herbicídneho přípravku /čs. pat. 120 858/.2-Phenyl-4,5-dichloropyridazone is the starting product in the preparation of the herbicidal formulation / cs. pat. 120,858 /.
Až doteraz bolí známe spósoby pripravy 2-fenyl-4,5-dichlórpyridazín-3“ónu například reakciou mukochldrovej kyseliny a fenylhydrazínhydrochloridu vo vodě za přítomnosti uhličitanu sodného, ďalej reakciou mukochlórovej kyseliny a fenylhydrazínu v prostředí zriedenej kyšeiny solnej /brit.pat. 881 616, franc. pat. 1 216 605/ pričom sa vzniknutý produkt izoluje fíltráciou.Hitherto known processes for the preparation of 2-phenyl-4,5-dichloropyridazin-3-one have been hindered, for example by reaction of mucochluric acid and phenylhydrazine hydrochloride in water in the presence of sodium carbonate, followed by reaction of mucochloric acid and phenylhydrazine in dilute saline / brit.pat. 881 616, French. pat. 1,216,605), wherein the resulting product is isolated by filtration.
Postupom podlá vynálezu sa 2-fenyl-4,5-dichlórpyrídazín-3-ón připravuje z 2-fenyl -4-amíno-5-chlórpyridazín-3-ónu, ktorý sa izoluje ako odpad /čs. pat. 122 103/ pri výrobě herbicídného přípravku do cukrovej řepy s účinnou látkou 2-fenyl-4-chlór-5-amínopyridazín-3-ónu /čs. pat. 120 858/.According to the process of the invention, 2-phenyl-4,5-dichloropyridazin-3-one is prepared from 2-phenyl-4-amino-5-chloropyridazin-3-one, which is isolated as a waste. pat. 122 103) in the preparation of a herbicidal preparation for sugar beets with the active substance 2-phenyl-4-chloro-5-aminopyridazin-3-one (cs. pat. 120,858 /.
Technicky sa odpad jednoduchou operáciou dá přečistit a tak získat 2-feny1-4-amíno-5-chlórpyridazín-3-ón o vysokej čistotě.Technically, the waste can be purified by a simple operation to obtain 2-phenyl-4-amino-5-chloropyridazin-3-one of high purity.
Je známe, že pósobením dusitanu sodného v prostředí kyseliny chlorovodíkovej na 2-fenyl-4-amíno-5-chldrpyridazín-3-on vzniká 2-fenyl-3,5-dioxo-4-diazopyridazín, z ktorého pósobením'chloridov médi sa získá 2-fenyl-4-chlór-5-hydroxypyridazín-3-ón.It is known that treatment of sodium nitrite in hydrochloric acid with 2-phenyl-4-amino-5-chloropyridazin-3-one results in the formation of 2-phenyl-3,5-dioxo-4-diazopyridazine from which treatment of the chloride with the medium yields 2-phenyl-4-chloro-5-hydroxypyridazine-3-one.
Teraz sa zistil spósob výroby 2-fenyl-4,5-díchlorpyridazín-3-ónu pósobením dusitanu sodného na 2-feny1-4-amíno-5-chlórpyrídazín-3-ón v prostředí kyseliny chlorovodíkóvej alebo jej zmesi s kyselinou octovou pri teplote -15°C až +50 °C za přítomnosti chloridu meďného v množstve 0,1 ažWe have now found a process for preparing 2-phenyl-4,5-dichloropyridazin-3-one by reacting sodium nitrite to 2-phenyl-4-amino-5-chloropyridazin-3-one in hydrochloric acid or a mixture thereof with acetic acid at - 15 ° C to + 50 ° C in the presence of copper (I) chloride in an amount of 0.1 to 15 ° C
1,5 molov na 1 mól 2-fenyl-4-amíno-5-chlórpyridazín-3-ónu.1.5 moles per mole of 2-phenyl-4-amino-5-chloropyridazin-3-one.
Najvačší význam výroby 2-feny1-4,5-dichlórpyridazín-3-ónu spósobom podlá vynálezu spočívá v jednoduchej príprave a hlavně vo využití odpadového 2-fenyl-4-amíno-5-chlórpyridazín-3-ónu pre túto výrobu.The greatest importance of the preparation of 2-phenyl-4,5-dichloropyridazin-3-one according to the invention lies in the simple preparation and mainly in the use of waste 2-phenyl-4-amino-5-chloropyridazin-3-one for this production.
Následujúce příklady ozrejmujú, ale v ničom neobmedzujú predmet vynálezu. Příklad 1 ?Zmee.11,1 g 1-fenyl-4-amíno-5-chlórpyrida zín-3-ónu, 100 ml kyseliny chlorovodíkovej a 2,5 g chloridu meďného sa ochladilo na -15 °C. Za intenzívneho miešania sa po častiach přidalo 10,3 g práškového dusitanu sodného počas 2 hodin pri teplote -15 °C až -10 °C reakčnej zmesi.The following examples illustrate but do not limit the scope of the invention. EXAMPLE 1 A mixture of 11.1 g of 1-phenyl-4-amino-5-chloropyridin-3-one, 100 ml of hydrochloric acid and 2.5 g of cuprous chloride was cooled to -15 ° C. With vigorous stirring, 10.3 g of sodium nitrite powder was added portionwise over 2 hours at -15 ° C to -10 ° C of the reaction mixture.
Reakčná zmes sa potom postupné vyhriala na 20 až 25 °C a udržovala sa pri uvedenej teplote 2 hodiny. Calšiu 1 hodinu sa udržova la reakčná zmes pri teplote 90 °C po predchádzajucom vyhriatí. Po ochladeni reakčnej zmesi na 20 °G přidalo sa 100 ml vody a pevný podiel sa odfiltroval. Z technického produktu přítomný 2-fenyl-4-chlór-5-hydroxypyridazín-3-ón vznikajúci ako vedlajší produkt sa odstranil rozpuštěním vo vodnom roztoku NaOH. Týmto spósobom sa získalo 4,8 gramu technického 2-fenyl-4,5-dichlórpyridazín-3-ónu s b. t. 156 až 162 °C čistoty 94,1 Z.The reaction mixture was then gradually warmed to 20-25 ° C and held at that temperature for 2 hours. The reaction mixture was maintained at 90 ° C for 1 h after the previous heating. After cooling the reaction mixture to 20 ° C, 100 ml of water was added and the solid was filtered off. The 2-phenyl-4-chloro-5-hydroxypyridazin-3-one present as a byproduct from the technical product was removed by dissolution in aqueous NaOH. 4.8 g of technical 2-phenyl-4,5-dichloropyridazin-3-one with b. t. 156-162 ° C of purity 94.1 Z.
Příklad 2Example 2
K zmesi 11,1 g 2-fenyl-4-amíno-5-chlór196105 pyridazln-3-ónu, 100 ml koncentrovanéj kyseliny chlorovodíkovej, 50 ml kyseliny octovej a 5,4 g chloridu meďného, za intenzívneho miešania pri teplote zmesi 20 aŽ 25 °C po čaštiach sa přidalo 10,3 g dusitanu sodného počas 2 hodin. Reakčná zmes sa potom miešala cfalšie 2 hodiny pri uvedenej teplote.To a mixture of 11.1 g of 2-phenyl-4-amino-5-chloro-6,105 pyridazin-3-one, 100 ml of concentrated hydrochloric acid, 50 ml of acetic acid and 5.4 g of cuprous chloride, with vigorous stirring at a temperature of 20-25 ° C 10.3 g of sodium nitrite was added in portions over 2 hours. The reaction mixture was then stirred for a further 2 hours at this temperature.
Po zriedení s 100 ml vody pevný podíel sa odfiltroval* Získalo sa 8,6 g technického 2-fenyl-4,5-dichlórpyridazín-3-ónu s b, t.After dilution with 100 ml of water, the solid was filtered off. 8.6 g of technical 2-phenyl-4,5-dichloropyridazin-3-one with b, m.p.
158 až 162 °C o čistotě 96i7 X.158-162 ° C with a purity of 96i7 X.
Příklad 3Example 3
K zmesi 11,1 g 2-fenyl-4-amino-5-chlór-To a mixture of 11.1 g of 2-phenyl-4-amino-5-chloro-
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Application Number | Priority Date | Filing Date | Title |
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CS189078A CS196105B1 (en) | 1978-03-24 | 1978-03-24 | Process for preparing 2-phenyl-4,5-dichlorpyridazin-3-one |
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CS189078A CS196105B1 (en) | 1978-03-24 | 1978-03-24 | Process for preparing 2-phenyl-4,5-dichlorpyridazin-3-one |
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1978
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