CS227947B1 - Production of 4 amino-1-phenyl-5-chlor-6-oxo-1h-pyridazine - Google Patents
Production of 4 amino-1-phenyl-5-chlor-6-oxo-1h-pyridazine Download PDFInfo
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- CS227947B1 CS227947B1 CS809582A CS809582A CS227947B1 CS 227947 B1 CS227947 B1 CS 227947B1 CS 809582 A CS809582 A CS 809582A CS 809582 A CS809582 A CS 809582A CS 227947 B1 CS227947 B1 CS 227947B1
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- oxo
- phenyl
- pyridazine
- amino
- chloro
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- 238000004519 manufacturing process Methods 0.000 title claims description 7
- XGZIUJAUPPHEGB-UHFFFAOYSA-N 6-amino-4-chloro-2-phenylpyridazin-3-one Chemical compound NC1=NN(C(C(=C1)Cl)=O)C1=CC=CC=C1 XGZIUJAUPPHEGB-UHFFFAOYSA-N 0.000 title 1
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- -1 NH ^ Inorganic materials 0.000 claims 1
- 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 description 14
- 238000000034 method Methods 0.000 description 9
- 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 description 7
- 239000000203 mixture Substances 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- 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
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229940077386 sodium benzenesulfonate Drugs 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Vynález sa týká spósobu výroby 4-amino-l-fenyÍ-5-chlór-6-oxo-lH-pyridazínu reakoiou 4,5-dichlór-l-fenyl-6-oxo-lH-pyridazínu s plynným amoniakom pri teplote udržujtícej reakčntí zmes vo formě taveniny, za přítomnosti katalyzátore.The present invention relates to a process for preparing 4-amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine by reacting 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine with ammonia gas at a temperature maintaining the reaction mixture. in the form of a melt, in the presence of a catalyst.
4-amino-l-fenyl-5-chlór-6-oxo-lH-pyridazín je herbicid určený predovšetkým na selektivně nlčenie burťn v cukrovéj repe /Burex, Pyramín/.4-Amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine is a herbicide intended primarily for selectively controlling the sugar beet (Burex, Pyramine).
Doteraz stí známe spósoby výroby 4-amino-l-fenyl-5-chlór-6-oxo-lH-pyridazínu vo vodnom prostředí /brit. pat. č. 871 674, EP 28-359/ ako aj v organických rozpdšťadláah /NDR pat. č. 131 172/.Hitherto known processes for the preparation of 4-amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine in aqueous medium / brit. pat. no. 871 674, EP 28-359] as well as in organic solvents (GDR). no. 131 172 /.
Dalšie známe postupy výroby 4-amino-l-fenyl-5-chlór-6-oxo-lH-pyridazínu spočívajú v aminácii 4,5-dichlór-l-fenyl-6-oxo-lH-pyridazínu plynným amoniakom pri teplote udržujtícej reakčntí zmes vo formě taveniny pričom sa využívá vyšší Specifický výkon aparatiíry ako aj možnost pracovali s poměrně malým prébytkom čpavku /čs. pat. 120 858, čs, aut. osv. 189 538/. Predmetom ČB. AO 208 446 je spósob výroby 4-amino-l-fenyl-5-chlór-6-oxo-lH-pyridazínu už popísaným postupom za přítomnosti močoviny.Other known processes for preparing 4-amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine include amination of 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine with ammonia gas at the temperature maintaining the reaction mixture. in the form of a melt, utilizing a higher specific power of the apparatus as well as the possibility to work with a relatively small excess of ammonia / MS. pat. 120 858, MS, aut. lighting. 189 538 /. Subject of BW. AO 208 446 is a process for preparing 4-amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine as described above in the presence of urea.
Spósob výroby 4-amlno-l-fenyl-5-ch}.ór-6-oxo-lH-pyridazínu vo formě taveniny má aj niektoré nedostatky.The process for preparing 4-amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine as a melt also has some drawbacks.
Je to například poměrně dlhá reakčná doba a hlavně vysoký obsah neaktívneho izoméru, t. j. 5-amino-l-fenyl-4-chlór-6-oxo-lH-pyridazínu v technickom produkte, ktorý představuje cca 20 až 24 % hmotnosti.This is, for example, a relatively long reaction time and, in particular, a high content of the inactive isomer, i. j. 5-amino-1-phenyl-4-chloro-6-oxo-1H-pyridazine in an industrial product which represents about 20 to 24% by weight.
Teraz sa zistil spósob výroby 4-amino-l-fenyl-5-chlór-6-oxo-lH-pyridazínu reakoiou 4,5-dichlór-l-fenyl-6-oxo-lH-pyridazínu s plynným amoniakom, připadne v přítomnosti sulfitového výluhu, močoviny alebo ich zmesi, pri teplote udržujúcej reakčnú zmes vo formě taveniny podlá vynálezu.We have now found a process for preparing 4-amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine by reacting 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine with ammonia gas, optionally in the presence of sulfite leach, urea, or a mixture thereof, at a temperature maintaining the melt-form reaction mixture of the invention.
Podstata vynálezu spočívá v tom, že reakcia sa uskutoční v přítomnosti katalyzátora pri reakčnej teplote 170 až 220 °C, pričom mólový poměr 4,5-dichlór -l-fenyl-6-oxo-lH-pyridazínu a katalyzátora je 1:0,01 až 0,5,SUMMARY OF THE INVENTION The reaction is carried out in the presence of a catalyst at a reaction temperature of 170 to 220 ° C, wherein the molar ratio of 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine to catalyst is 1: 0.01 up to 0,5,
Katalyzátorom je podlá vynálezu zlúčenina všeobecného vzorea XThe catalyst of the present invention is a compound of formula (X)
R - COOX /1/ v ktorom R^ znamená vodík, alkyl s 1 až 4 atómami uhlíka, aralkyl, fenoxyalkyl, X znamená vodík, skupinu -NH^ alebo alkalický kov.R = COOX (1) wherein R R is hydrogen, alkyl of 1 to 4 carbon atoms, aralkyl, phenoxyalkyl, X is hydrogen, -NH ^ or an alkali metal.
Katalyzátorom móže byt tiež zlúčenina všeobecného vzorea II,The catalyst may also be a compound of formula II,
COOX /11/ v ktorom znamená vodík, halogén alebo hydroxyskupinu, X má už uvedený význam, alebo zlúčenina všeobecného vzorea III, \^803χ v ktorom znamená vodík, skupinu OH, X má už uvedený význam.COOX / 11 / wherein is hydrogen, halogen or hydroxy, X is as defined above, or a compound of vzorea III, \ ^ χ 3 0 8 which is H, OH, X is as defined above.
Výhodou nového postupu je skutočnosť, že sa zvýši reakčná rýohlost oproti doterajším spósobom přípravy 4-amino-l-fenyl-5-chlór-6-oxo-lH-pyridazínu vo formě' taveniny, čo představuje zníženie energetických požiadaviek a možnost zvyšovania kapacity výroby. Dalej je potřebné zdóraznit, že podlá tohto postupu sa zníži obsah 5-amino-l-fenyl-4-chlór-6-oxO-lH-pyridazínu, t. j. neaktívneho izoméru v technickom produkte, čo znamená zvýšenie výtažku 4-amino-l-fenyl-5-chlór-6-oxo-ΙΗ-pyridazinu.The advantage of the new process is that the reaction rate will increase over the prior art processes for preparing 4-amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine in the form of a melt, which reduces energy requirements and increases production capacity. Further, it should be noted that this procedure reduces the content of 5-amino-1-phenyl-4-chloro-6-oxo-1H-pyridazine, i. j. of the inactive isomer in the technical product, which means an increase in the yield of 4-amino-1-phenyl-5-chloro-6-oxo-ΙΗ-pyridazine.
Nasledujúce příklady ozrejmujú, ale neobmedzujú predmet vynálezu.The following examples illustrate but do not limit the scope of the invention.
Příklad 1Example 1
Do reaktora válcovitého tvaru o objeme 150 ml sa nadávkovalo 50 g čistého 4,5-dichlór-l-fenyl-6-oxo-lH-pyridazínu, 1 g sulfitového výluhu a 2,5 g octanu draselného·.· Pri 180 °C sa zavádzal amoniak do reakčnej zmesi takou rýchlostou, aby dávkované množstvo bolo v malom přebytku voči spotrebe. Po 3 hodinách bola reakcia ukončená. Ochladená tavenina sa rozdrtila a přítomný chlorid amónny sa vymyl vodou.A 150 ml cylindrical reactor was charged with 50 g of pure 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine, 1 g of sulfite extract and 2.5 g of potassium acetate. introduced ammonia into the reaction mixture at a rate such that the feed rate was in a small excess over consumption. After 3 hours the reaction was complete. The cooled melt was crushed and the ammonium chloride present was washed with water.
Výsledný technický produkt hmotnosti 43,2 g málo následovně zloženie stanovené kvapalinovu chromatografiou: 81,6 % 4-amino-l-fenyl-5-chlór-6-oxo-lH-pyridazínu a 13,6 % 5-amino-l-fenyl-4-chlór-6-oxo-lH-paridazínu.The resulting technical product weighing 43.2 g little following the composition determined by liquid chromatography: 81.6% 4-amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine and 13.6% 5-amino-1-phenyl 4-chloro-6-oxo-paridazínu.
Příklad 2Example 2
Do aparatúry popísanej v příklade 1 sa nadávkovalo 51,7 g 96,7 %-ného 4,5-dichlór-1-fenyl-6-oxo-lH-pyridazínu a 2 g kyseliny maslovej. Postupom už popísaným v příklade 1 sa získalo 43,1 g technického produktu o zložení 79,5 % 4-amino-l-fenyl-5-chlór-6-oxo-lH-pyridazínu, 13,9 % 5-amlno-l-fenyl-4-chlór-6-oxo-lH-pyridazínu a 0,6 % nezreagovaného 4,5-dlchlór-l-fenyl-6-oxo-lH-pyridazínu.51.7 g of 96.7% 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine and 2 g of butyric acid were metered into the apparatus described in Example 1. Following the procedure described in Example 1, 43.1 g of technical product were obtained, consisting of 79.5% of 4-amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine, 13.9% of 5-amino-1- phenyl-4-chloro-6-oxo-1H-pyridazine and 0.6% unreacted 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine.
Příklad 3Example 3
Do aparatúry popísanej v příklade 1 sa nadávkovalo 51,7 g 96,7 %-ného 4,5-dichlór-l-fenyl-6-oxo-lH-pyridazínu, 1 g sulfltového výluhu a 2,5 g fenoxyoctovej kyseliny. Postupom popísaným už v příklade 1 sa získalo 45 g technického produktu o zložení: 78,7 % 4-amino-l-fenyl-5-chlór-6-oxo-lH-pyridazínu, 16,6 % 5-amino-l-fenyl-4-chlór-6-oxo-lH-pyridazínu.51.7 g of 96.7% 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine, 1 g of sulphite extract and 2.5 g of phenoxyacetic acid were metered into the apparatus described in Example 1. As described in Example 1, 45 g of a technical product having the following composition were obtained: 78.7% 4-amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine, 16.6% 5-amino-1-phenyl 4-chloro-6-oxo-pyridazine.
Příklad 4Example 4
Do aparatúry popísanej v příklade 1 sa nadávkovalo 50 g 4,5-dichlór-l-fenyl-6-οχο-ΙΗpyridazínu, 1 g sulfltového výluhu a 7,5 g draselnej soli benzoovej kyseliny. Pri 200 °C sa zavádzal amoniak do reakčnej zmesi. Po 2 hodinách bola reakcia ukončená. Ochladená tavenina sa rozdrtila a přítomný chlorid amónny sa vymyl vodou.50 g of 4,5-dichloro-1-phenyl-6-oxo-pyridazine, 1 g of sulphite extract and 7.5 g of potassium benzoic acid salt were metered into the apparatus described in Example 1. Ammonia was introduced into the reaction mixture at 200 ° C. After 2 hours the reaction was complete. The cooled melt was crushed and the ammonium chloride present was washed with water.
Výsledný technický produkt o hmotnosti 42,1 g málo zloženie: 82,2 % 4-amino-l-fenyl-5-chlór-6-oxo-lH-pyridazínu, 11,8 % 5-amino-l-fenyl-4-chlór-6-oxo-lH-pyridazínu a 0,2 i nezreagovaného 4,5-dichlór-l-fenyl-6-oxo-lH-pyridazínu.Resulting technical product weighing 42.1 g little composition: 82.2% 4-amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine, 11.8% 5-amino-1-phenyl-4- chloro-6-oxo-1H-pyridazine and 0.2% unreacted 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine.
Příklad 5Example 5
Postupom a navážkami ako v příklade 4 s rozdlelom, že namiesto draselnej soli benzoovej kyseliny sa použilo 5 g 4-hydroxybenzoovej kyseliny sa získalo 44,9 g technického produktu o zložení: 81,9 % 4-amino-l-fenyl-5-chlór-6-oxo-lH-pýridazínu, 13,2 % 5-amino-l-fenyl-4-chlór-6-oxo-lH-pyridazínu a 0,2 % nezreagovaného 4,5-dichlór-l-fenyl-6-oxo-lH-pyridazínu.Using the procedure and the weightings as in Example 4, with the difference that 5 g of 4-hydroxybenzoic acid was used instead of the potassium benzoic acid salt, 44.9 g of the technical product was obtained having the following composition: 81.9% 4-amino-1-phenyl-5-chloro 6-oxo-1H-pyridazine, 13.2% 5-amino-1-phenyl-4-chloro-6-oxo-1H-pyridazine and 0.2% unreacted 4,5-dichloro-1-phenyl-6- oxo-pyridazine.
Príklad6Example 6
Postupom a navážkami ako v příklade 4 s rozdielom. Že namiesto draselnej soli benzoovej kyseliny sa použilo 2 g 2-chlorbenzoovej kyseliny, sa získalo 45,4 g technického produktu o zložení: 79,8 % 4-amino-l-fenyl-5-chlór-6-oxo-lH-pyridazínu, 15,4 % 5-amino-l-fenyl-4~ -chlór-6-oxo-lH-pyrldazínu a 0,9 % nezreagovaného 4,5-dichlór-l-f enyl-6-oxo-lH-pyridazínu.·Using the procedures and weights as in Example 4 with the difference. Using 2 g of 2-chlorobenzoic acid in place of the benzoic acid potassium salt yielded 45.4 g of technical product having the following composition: 79.8% 4-amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine, 15.4% of 5-amino-1-phenyl-4-chloro-6-oxo-1H-pyrldazine and 0.9% of unreacted 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine.
Příklad 7Example 7
Do aparatúry popísanej v příklade 1 sa navážilo 50,6 g 98,7 %-ného 4,5-dichlór-l-fenyl-6-oxo-lH-pyridazínu, 0,5 g sulfitového výluhu, 2,5 g benzénsulfonanu sodného a 0,5 g močoviny. Další postup sa uskutočnil podlá příkladu 1. Získalo sa 46,5 g technického produktu o zložení: 80,6 % 4-amino-l-fenyl-5-chlór-6-oxo-lH-pyridazínu, 18,3 % 5-amino-l-fenyl-4-chlór-6-oxo-lH-pyridazínu a 0,4 % nezreagovaného 4,5-dichlór-l-fenyl-6-oxo-lH-pyridazínu.The apparatus described in Example 1 was weighed with 50.6 g of 98.7% 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine, 0.5 g of sulphite liquor, 2.5 g of sodium benzenesulfonate and 0.5 g urea. The further procedure was carried out according to Example 1. 46.5 g of technical product were obtained having the following composition: 80.6% 4-amino-1-phenyl-5-chloro-6-oxo-1H-pyridazine, 18.3% 5-amino -1-phenyl-4-chloro-6-oxo-1H-pyridazine and 0.4% unreacted 4,5-dichloro-1-phenyl-6-oxo-1H-pyridazine.
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| CS809582A CS227947B1 (en) | 1982-11-15 | 1982-11-15 | Production of 4 amino-1-phenyl-5-chlor-6-oxo-1h-pyridazine |
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| Application Number | Priority Date | Filing Date | Title |
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| CS809582A CS227947B1 (en) | 1982-11-15 | 1982-11-15 | Production of 4 amino-1-phenyl-5-chlor-6-oxo-1h-pyridazine |
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| CS227947B1 true CS227947B1 (en) | 1984-05-14 |
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| CS809582A CS227947B1 (en) | 1982-11-15 | 1982-11-15 | Production of 4 amino-1-phenyl-5-chlor-6-oxo-1h-pyridazine |
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1982
- 1982-11-15 CS CS809582A patent/CS227947B1/en unknown
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