CS229443B1 - Method of preparing 4,5-dichloro-1-phenyl-6-oxo-1h-pyridazine - Google Patents
Method of preparing 4,5-dichloro-1-phenyl-6-oxo-1h-pyridazine Download PDFInfo
- Publication number
- CS229443B1 CS229443B1 CS934982A CS934982A CS229443B1 CS 229443 B1 CS229443 B1 CS 229443B1 CS 934982 A CS934982 A CS 934982A CS 934982 A CS934982 A CS 934982A CS 229443 B1 CS229443 B1 CS 229443B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- pyridazine
- dichloro
- oxo
- phenyl
- phenylhydrazine
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 7
- 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 description 9
- 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 description 10
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 8
- 229940067157 phenylhydrazine Drugs 0.000 claims description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- VUTBELPREDJDDH-UHFFFAOYSA-N 4-amino-5-hydroxymethyl-2-methylpyrimidine Chemical compound CC1=NC=C(CO)C(N)=N1 VUTBELPREDJDDH-UHFFFAOYSA-N 0.000 description 1
- BMKCLGBWAXSQQL-UHFFFAOYSA-N 5,6-dichloro-2-phenylpyridazin-3-one Chemical compound N1=C(Cl)C(Cl)=CC(=O)N1C1=CC=CC=C1 BMKCLGBWAXSQQL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000009835 boiling Methods 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
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
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- Plural Heterocyclic Compounds (AREA)
Description
Vynález sa týká spósobu výroby 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu.The present invention relates to a process for the preparation of 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine.
4,5-dichlór-l-fenyl-6-oxo-1H-pyridazín je medziprodukt pri výrobě herbicídného přípravku (Burex, Pyramín).4,5-Dichloro-1-phenyl-6-oxo-1H-pyridazine is an intermediate in the manufacture of a herbicidal preparation (Burex, Pyramine).
Doteraz sú známe viaceré spósoby přípravy 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu.Several methods for the preparation of 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine are known to date.
PodTa DAS 1,086238 příprava sa uskutoční reakciou kyseliny mukochlórovej a fenylhydrazínu v prostředí organického rozpúšťadla, pričom reakciou vytvořená voda sa odstraňuje z reakčného prostredia vo formě azeotropu. čs. AO 205 592 popisuje reakciu kyseliny mukochlórovej s f enylhydrazínoin v zmesi organického nepolárného rozpúšťadla a vody.According to DAS 1.086238, the preparation is carried out by reacting mucochloric acid and phenylhydrazine in an organic solvent medium, wherein the reaction water formed is removed from the reaction medium in the form of an azeotrope. MS. AO 205 592 describes the reaction of mucochloric acid with phenylhydrazinoin in a mixture of an organic non-polar solvent and water.
Ďalšie známe spósoby sú založené na reakcii kyseliny mukochlórovej a fenylhydrazínhydrochloridu vo vodnom prostředí. PodTa USA pat. č. 2,628.18b sa uskutoční reakcia mukochló rovej kyseliny a fenylhydrazínhydrochloridu vo vodě za přítomnosti uhličitanu sodného, pričom vzniknutý produkt fenylhydrazón kyseliny mukochlórovej sa izoluje a varom v ladovej kyselinp octovej sa prevedie na 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazín.Other known methods are based on the reaction of mucochloric acid and phenylhydrazine hydrochloride in an aqueous medium. According to US Pat. no. 2,628.18b is carried out by reacting mucochloric acid and phenylhydrazine hydrochloride in water in the presence of sodium carbonate, isolating the resulting phenylhydrazone mucochloric acid product and boiling in glacial acetic acid to 4,5-dichloro-1-phenyl-6-oxo-1H- pyridazine.
Ďalší spósob výroby sa uskutoční reakciou mukochlórovej kyseliny a fenylhydrazínu v prostředí zriedenej minerálnej kyseliny (Brit. pat. č. 881.616).Another production method is carried out by reacting mucochloric acid and phenylhydrazine in a dilute mineral acid medium (British Pat. No. 881,616).
Predmetom Ss. AO 220 299 je příprava 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu reakciou kyseliny mukochlórovej a fenylhydrazínu v prostředí zriedenej kyseliny chlorovodíkovej pri přísné vymedzenom mólovom pomere fenylhydrazínu k chlorovodíku, pri ktorom sa dosiahne vysoký výťažok 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu.Subject Ss. AO 220 299 is the preparation of 4,5-dichloro-1-phenyl-6-oxo-1 H -pyridazine by reacting mucochloric acid and phenylhydrazine in dilute hydrochloric acid at a strictly defined molar ratio of phenylhydrazine to hydrogen chloride, resulting in a high yield of 4.5 dichloro-1-phenyl-6-oxo-1 H-pyridazine.
Příprava 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu podl’a uvedeného AO sa uskutočňuje šaržovite t. j. diskontinuálne.The preparation of 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine according to the above AO is carried out batchwise. j. discontinuous.
Teraz sa našiel spfisob výroby 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu reakciou kyseliny mukochlórovej a fenylhydrazínu v prostředí zriedenej kyseliny chlorovodíkovej při teplote 30 až 100 °C podlá vynálezu, ktorého podstata spočívá v tom, že reakcia sa uskutoční kontinuálně v prietokovom reaktore pri vzájomnom mólovom pomere Chlorovodíka k fenylhydrazínu 2,2 až 2,5.We have now found a process for the preparation of 4,5-dichloro-1-phenyl-6-oxo-1 H -pyridazine by reacting mucochloric acid and phenylhydrazine in dilute hydrochloric acid at a temperature of 30 to 100 ° C according to the invention. The reaction is carried out continuously in a flow reactor at a relative molar ratio of hydrogen chloride to phenylhydrazine of 2.2 to 2.5.
Výhoda nového postupu výroby i,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu spočívá v jednoduchosti uskutočnenia, v energetiokej výhodnosti voči diskontinuálnemu spfisobu výroby s možnosťou kontinuálnej separácie produktu z reakčného prostredia, čím sa zamedzí styk praeovnlkov s uvedenou látkou vyvolávajúcu kožné onemocněnie.The advantage of the novel process for the preparation of 1,5-dichloro-1-phenyl-6-oxo-1H-pyridazine lies in its ease of execution, its energy advantage over the batch process, with the possibility of continuous separation of the product from the reaction medium. causing skin disease.
Následujúci příklad ilustruje, ale neóbmedzuje predmet vynálezu.The following example illustrates but does not limit the invention.
PříkladExample
Do prietokového reaktora pozostávajúceho z troch kotlov vzájomné spojených v kaskádě a opatřených miešadlom sa dávkovalo hodinové 12,5 kg 7 %-ného vodného roztoku kyseliny mukochlórovej o teplote 70 °C, 10,6 kg vodného roztoku 7 % fenylhydrazínhydrochlóridu a 0,6 kg 31 %-nej kyseliny chlorovodíkovej. Reakčná zmes sa udržiavala v reaktore při teplote 95 °G a zádrž bola 1 h. Technický produkt 4,5-dichlór-1-fenyl-6-oxo-1H-pyridazínu sa izoloval filtráciou.12.5 kg of a 7% aqueous solution of mucochloric acid at 70 ° C, 10.6 kg of an aqueous solution of 7% phenylhydrazine hydrochloride and 0.6 kg 31 were charged to the flow reactor consisting of three boilers connected together in a cascade and equipped with a stirrer. % hydrochloric acid. The reaction mixture was held in the reactor at 95 ° C and held for 1 h. Technical product 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine was isolated by filtration.
Za 1 h sa získalo 1,22 kg produktu o čistotě 99,1 %. Výťažok představuje 96,03 % teorie.1.22 kg of product with a purity of 99.1% were obtained in 1 hour. Yield 96.03% of theory.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS934982A CS229443B1 (en) | 1982-12-20 | 1982-12-20 | Method of preparing 4,5-dichloro-1-phenyl-6-oxo-1h-pyridazine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS934982A CS229443B1 (en) | 1982-12-20 | 1982-12-20 | Method of preparing 4,5-dichloro-1-phenyl-6-oxo-1h-pyridazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS229443B1 true CS229443B1 (en) | 1984-06-18 |
Family
ID=5444099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS934982A CS229443B1 (en) | 1982-12-20 | 1982-12-20 | Method of preparing 4,5-dichloro-1-phenyl-6-oxo-1h-pyridazine |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS229443B1 (en) |
-
1982
- 1982-12-20 CS CS934982A patent/CS229443B1/en unknown
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