CS220299B1 - Method of producing 1-phenyl-4,5-dichloro-6-oxo-1h-pyridazine - Google Patents
Method of producing 1-phenyl-4,5-dichloro-6-oxo-1h-pyridazine Download PDFInfo
- Publication number
- CS220299B1 CS220299B1 CS44282A CS44282A CS220299B1 CS 220299 B1 CS220299 B1 CS 220299B1 CS 44282 A CS44282 A CS 44282A CS 44282 A CS44282 A CS 44282A CS 220299 B1 CS220299 B1 CS 220299B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- pyridazine
- dichloro
- oxo
- phenyl
- phenylhydrazine
- Prior art date
Links
- 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 abstract description 10
- 238000000034 method Methods 0.000 title abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 19
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229940067157 phenylhydrazine Drugs 0.000 claims abstract description 15
- 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 claims abstract description 14
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 3
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 3
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SSDAKJLEKSSAMH-UHFFFAOYSA-N 2,4-dihydro-1h-pyridazin-3-one Chemical compound O=C1CC=CNN1 SSDAKJLEKSSAMH-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Abstract
Sposob výroby l-fenyl-4,5-dichlór-6-oxo- -lH-pyridazínu reakciou kyseliny mukochlórovej a fenylhydrazínu v prostředí zriedenej kyseliny chlorovodíkové]' pri vzájomnom mólovom pomere chlorovodíka k fenylhydrazínu 2,2 až 2,5 :1.The process for producing 1-phenyl-4,5-dichloro-6-oxo- 1H-pyridazine by reaction of mucochloric acid and phenylhydrazine in a dilute medium hydrochloric acid] mole ratio of hydrogen chloride to phenylhydrazine 2.2 to 2.5: 1.
Description
Vynález sa týká spósobu výroby 1-fenyl-4,5-dichlór-6-oxo-lH-pyridazínu.The present invention relates to a process for the preparation of 1-phenyl-4,5-dichloro-6-oxo-1H-pyridazine.
l-fenyl-4,5-dichlóť-6-oxo-lH-pyridazín je východiskovým produktom pri výrobě herbicídneho přípravků (čsl. patent 120 858).1-Phenyl-4,5-dichloro-6-oxo-1H-pyridazine is the starting product in the manufacture of herbicidal compositions (U.S. Patent 120,858).
Doteraz boli známe spósoby přípravy 1-fenyl-4,5-dichlór-6-óxo-lH-pyridazínu z kyseliny mukochlórovej a fenylhydrazínu v prostředí organického rozpúšťadla, pričom reakciou vytvořená voda sa odstraňuje z reakčného prostredia vo formě azeotropu (DAS 1086 238). Podlá čsl. aut. osvedčenia 205 592 reakcia kyseliny mukochlórovej a fenylhydrazínu prebieha v zmesi organického nepolárného rozpúšťadla a vody. Ďalšie známe spósoby sú založené na reakcii kyseliny mukochlórovej a fenylhydrazínhydrochloridu vo vodnom prostředí. Podfa USA patentu č. 2 628 181 sa uskutoční reakcia mukochlórovej kyseliny a fenylhydrazínhydrochloridu vo vodě za přítomnosti uhličitanu sodného, pričom vzniknutý produkt fenylhydrazón kyseliny mukochlórovej sa izoluje a varom v 1'adovej kyselině octovej sa prevedie na l-fenyl-4,5-dichlór-6-oxo-lH-pyridazín. Další známy spósob výroby sa uskutoční reakciou mukochlórovej kyseliny a fenylhydrazínu v prostředí zriedenej kyseliny chlorovodíkové j (brit. patent č. 881616). Ako je zřejmé z príkladovej časti tohto patentu, patent nevystihuje skutočnosť, že vysoké výtažky reakcie fenylhydrazínu s mukochlórovou kyselinou možno dosiahnuť len v přísné vymedzenom mólovom pomere medzi fenylhydrazínom a chlorovodíkom. Tak v příklade převedenou reakciou medzi fenylhydrazínom a mukochlórovou kyselinou, v prostředí kyseliny sofnej, při trojhodinovej reakčnej době a teplote reakčnej zmesi 90 až 100 °C dosahuje sa iba 78,5%-ný výťažok 1-fenyl-4,5-dichlór-6-oxo-lH-pyridazínu.Hitherto, methods for preparing 1-phenyl-4,5-dichloro-6-oxo-1H-pyridazine from mucochloric acid and phenylhydrazine in an organic solvent environment have been known, wherein the water formed by the reaction is removed from the reaction medium as an azeotrope (DAS 1086 238). Podlá čsl. aut. The reaction of mucochloric acid and phenylhydrazine is carried out in a mixture of an organic nonpolar solvent and water. Other known methods are based on the reaction of mucochloric acid and phenylhydrazine hydrochloride in an aqueous medium. According to U.S. Pat. No. 2,628,181, the reaction of mucochloric acid and phenylhydrazine hydrochloride in water in the presence of sodium carbonate is isolated and the resulting phenylhydrazone mucochloric acid product is isolated and boiled in 1-glacial acetic acid to 1-phenyl-4,5-dichloro-6-oxo H-pyridazine. Another known process is carried out by reacting mucochloric acid and phenylhydrazine in dilute hydrochloric acid (British Patent No. 881616). As is evident from the example section of this patent, the patent does not capture the fact that high yields of reaction of phenylhydrazine with mucochloric acid can only be achieved in a strictly defined molar ratio between phenylhydrazine and hydrogen chloride. Thus, by way of example, the reaction carried out between phenylhydrazine and mucochloric acid, in hydrochloric acid, at a reaction time of three hours and at a reaction temperature of 90 to 100 ° C yields only 78.5% yield of 1-phenyl-4,5-dichloro-6. oxo-lH-pyridazine.
Teraz sa zistilo, že pre dosiahnutie optimálneho výtažku ako i ovplyvnenie reakčnej rýchlosti pri príprave l-fenyl-4,5-dichlór-6-oxo-lH-pyridazínu reakciou kyseliny mukochlórovej a fenylhydrazínu v rovnakých mólových pomeroch v prostředí zriedenej kyseliny chlorovodíkové], najdóležitejším faktorom je vzájomný poměr chlorovodíka k fenylhydrazínu.It has now been found that for optimum yield as well as influencing the reaction rate in the preparation of 1-phenyl-4,5-dichloro-6-oxo-1H-pyridazine by reacting mucochloric acid and phenylhydrazine in the same molar ratios in dilute hydrochloric acid environment, the most important the factor is the relative ratio of hydrogen chloride to phenylhydrazine.
Podstata vynálezu spočívá v tom, že vzájomný mólový poměr chlorovodíka k fenylhydrazínu je 2,2 až 2,5 :1.The principle of the invention is that the relative molar ratio of hydrogen chloride to phenylhydrazine is 2.2 to 2.5: 1.
Hlavnou výhodou spósobu přípravy 1-fenyl-4,5-dichlór-6-oxo-lH-pyridazínu je vysoký výťažok l-fenyl-4,5-dichlór-6-oxo-lH-pyridazínu za poměrně krátku reakčnú dobu.A major advantage of the process for preparing 1-phenyl-4,5-dichloro-6-oxo-1H-pyridazine is the high yield of 1-phenyl-4,5-dichloro-6-oxo-1H-pyridazine in a relatively short reaction time.
Vplyv vzájomného mólového poměru chlorovodíka (HC1) k fenylhydrazínu (FH) na výťažok l-fenyl-4,5-dichlór-6-oxo-lH-pyridazínu (PCC) pri reakcii kyseliny mukochlórovej a fenyilhydrazínu v ekvimolových pomeroch pri reakčnej teplote 90 až 95 °C po dobu 10 minút uvádza nasledujúca tabulka.Effect of the relative molar ratio of hydrogen chloride (HCl) to phenylhydrazine (FH) on the yield of 1-phenyl-4,5-dichloro-6-oxo-1H-pyridazine (PCC) in the reaction of mucochloric acid and phenyilhydrazine in equimolar ratios at reaction temperatures of 90-95 ° C for 10 minutes is shown in the following table.
Mólový poměr HC1: FHMolar ratio HCl: FH
1,02 l;051.02 l; 05
2,02.0
2,22.2
2.5 3,02.5 3,0
3.5 4,03.5 4,0
Výťažok PCC (%)PCC yield (%)
81.9 83,481.9 83.4
86.9 90,8 90,8 86,1 85,0 83,486.9 90.8 90.8 86.1 85.0 83.4
Nasledujúce příklady ilustrujú ale neobmedzujú predmet vynálezu.The following examples illustrate but do not limit the invention.
Příklad 1Example 1
Do banky opatrenej miešadlom a spatným chladičom sa předložilo 36,3 g 93%-nej kyseliny mukochlórovej, 400 ml vody a 52,4 g 32%-nej kyseliny chlorovodíkové]'. Potom za miešania sa přidalo 21,6 g fenylhydrazínu a reakčná zmes sa vyhriala na 90 až 95 °C a pri tejto teplote sa udržala po dobu 30 minút. Po ochladení na 20 CC sa produkt izoloval filtráciou. Získalo sa 47,1 g l-fenyl-4,5-dichlór-6-oxo-lH-pyridazínu o čistotě 98,4 percenta. Výťažok představuje 96,05 % teórie.A flask equipped with a stirrer and a reflux condenser was charged with 36.3 g of 93% mucochloric acid, 400 ml of water and 52.4 g of 32% hydrochloric acid. Then, 21.6 g of phenylhydrazine was added with stirring and the reaction mixture was heated to 90-95 ° C and held at this temperature for 30 minutes. After cooling to 20 ° C, the product was isolated by filtration. 47.1 g of 1-phenyl-4,5-dichloro-6-oxo-1H-pyridazine of 98.4 percent purity were obtained. Yield 96.05% of theory.
Příklad 2Example 2
Do kotlá sa předložilo 187 kg 93%-nej kyseliny mukochlórovej a 300 1 vody. Za miešania sa přidalo 212,6 kg 7%-ného vodného roztoku fenylhydrazínhydrochloridu a 136 kg 36%-nej kyseliny chlorovodíkovej. Reakčná zmes sa vyhriala na 95 až 100 °C a udržovala sa pri tejto teplote po dobu 45 minút. Po ochladení zmesi na 20 až 25 °C sa pevný produkt odfiltroval. Získalo sa 247 kg technického l-fenyl-4,5-dichlór-6-oxo-ΙΗ-pyridazínu o čistotě 96,7 %.187 kg of 93% mucochloric acid and 300 L of water were charged to the boilers. While stirring, 212.6 kg of a 7% aqueous phenylhydrazine hydrochloride solution and 136 kg of 36% hydrochloric acid were added. The reaction mixture was heated to 95-100 ° C and held at this temperature for 45 minutes. After cooling the mixture to 20-25 ° C, the solid product was filtered off. 247 kg of technical 1-phenyl-4,5-dichloro-6-oxo-pyrid-pyridazine having a purity of 96.7% were obtained.
Výťažok představuje 96,2 % teórie.Yield 96.2% of theory.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS44282A CS220299B1 (en) | 1982-01-22 | 1982-01-22 | Method of producing 1-phenyl-4,5-dichloro-6-oxo-1h-pyridazine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS44282A CS220299B1 (en) | 1982-01-22 | 1982-01-22 | Method of producing 1-phenyl-4,5-dichloro-6-oxo-1h-pyridazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS220299B1 true CS220299B1 (en) | 1983-03-25 |
Family
ID=5336482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS44282A CS220299B1 (en) | 1982-01-22 | 1982-01-22 | Method of producing 1-phenyl-4,5-dichloro-6-oxo-1h-pyridazine |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS220299B1 (en) |
-
1982
- 1982-01-22 CS CS44282A patent/CS220299B1/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4670191A (en) | Process for the preparation of N-phosphonomethylglycine | |
| CS220299B1 (en) | Method of producing 1-phenyl-4,5-dichloro-6-oxo-1h-pyridazine | |
| JPH1067755A (en) | Production of 4,6-dihydroxypyrimidine | |
| EP0343597B1 (en) | Preparation of tris (2-cyanoethyl) amine | |
| US4275216A (en) | Process for preparing 4(5)-hydroxymethyl 5(4)-lower alkyl imidazoles | |
| JPS6127980A (en) | Preparation of hydroxyflavan compound | |
| US3360534A (en) | Method of producing a guanyl-o-alkylisourea salt | |
| US3249611A (en) | Novel method for the preparation of phthalazines | |
| US4299962A (en) | Process for synthesizing 2-sulphanilamido-3-methoxypyrazine | |
| JPS61286346A (en) | Production of 2,2-bis(4'-acryloyloxy-3',5'-dibromophenyl) propane | |
| US3636000A (en) | Method for preparing dithiourazole | |
| US3654292A (en) | Manufacture of 3 5-dichloro-2 6-difluoro - 4 - hydroxypyridine and salts thereof | |
| JPS5843972A (en) | Manufacture of dihydroxypropyltheophylline | |
| JP2708617B2 (en) | Method for producing 4,4-dialkyl-substituted thiazolidinethione | |
| JPH0745468B2 (en) | Process for producing tetrachlor-3-imino-isoindoline-1-one | |
| JPS6226274A (en) | Manufacture of 4(5)-hydroxymethyl-5(4)-methylimidazole | |
| JPS61140554A (en) | Use of alkyl n-maleylphenylalanate and manufacture | |
| JPS5928547B2 (en) | Process for producing 3-phenyl-viridazone-(6) | |
| SU1228785A3 (en) | Method of producing derivatives of hypoxanthine | |
| SU418035A1 (en) | Method for producing 3,4-diazaphenoxazine intra derivative | |
| SU388553A1 (en) | Process for preparing derivatives of isoindoline | |
| JPS5951251A (en) | Production method of benzyl cyanides | |
| JPS5832869A (en) | Synthesis of biscyclic iminoether compound | |
| JPS5933583B2 (en) | Production method of 1,4-naphthodinitrile | |
| JPH0572381B2 (en) |