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
- Publication number
- 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
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- phenyl
- amino
- dichloropyridazin
- chloropyridazin
- temperature
- Prior art date
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- VKWCOHVAHQOJGU-UHFFFAOYSA-N 4,5-dichloro-2-phenylpyridazin-3-one Chemical compound O=C1C(Cl)=C(Cl)C=NN1C1=CC=CC=C1 VKWCOHVAHQOJGU-UHFFFAOYSA-N 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 12
- HAKJEHJYRKVCIU-UHFFFAOYSA-N 4-amino-5-chloro-2-phenylpyridazin-3-one Chemical compound O=C1C(N)=C(Cl)C=NN1C1=CC=CC=C1 HAKJEHJYRKVCIU-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 235000010288 sodium nitrite Nutrition 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HYZCDNSVEFVQSZ-UHFFFAOYSA-N 4-chloro-5-hydroxy-2-phenylpyridazin-3-one Chemical compound O=C1C(Cl)=C(O)C=NN1C1=CC=CC=C1 HYZCDNSVEFVQSZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LUMLZKVIXLWTCI-NSCUHMNNSA-N (e)-2,3-dichloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(/Cl)C=O LUMLZKVIXLWTCI-NSCUHMNNSA-N 0.000 description 1
- -1 1-phenyl-4-amino-5-chloropyridin-3-one Chemical compound 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- JIGHLIVNFSJEJF-UHFFFAOYSA-N 4-diazonio-5-oxo-2-phenylpyridazin-3-olate Chemical compound [O-]C1=C([N+]#N)C(=O)C=NN1C1=CC=CC=C1 JIGHLIVNFSJEJF-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- TVPRCLHSULCNLV-UHFFFAOYSA-N pyridazin-3-one Chemical compound O=C1C=CC=N[N]1 TVPRCLHSULCNLV-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
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-
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS189078A CS196105B1 (en) | 1978-03-24 | 1978-03-24 | Process for preparing 2-phenyl-4,5-dichlorpyridazin-3-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS189078A CS196105B1 (en) | 1978-03-24 | 1978-03-24 | Process for preparing 2-phenyl-4,5-dichlorpyridazin-3-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196105B1 true CS196105B1 (en) | 1980-03-31 |
Family
ID=5354400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS189078A CS196105B1 (en) | 1978-03-24 | 1978-03-24 | Process for preparing 2-phenyl-4,5-dichlorpyridazin-3-one |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS196105B1 (en) |
-
1978
- 1978-03-24 CS CS189078A patent/CS196105B1/en unknown
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