CS255243B1 - 5-brom-6-(4-pentyloxyphenyl)-3-(2h)pyridazinon and process for preparing the same - Google Patents
5-brom-6-(4-pentyloxyphenyl)-3-(2h)pyridazinon and process for preparing the same Download PDFInfo
- Publication number
- CS255243B1 CS255243B1 CS867564A CS756486A CS255243B1 CS 255243 B1 CS255243 B1 CS 255243B1 CS 867564 A CS867564 A CS 867564A CS 756486 A CS756486 A CS 756486A CS 255243 B1 CS255243 B1 CS 255243B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- pentyloxyphenyl
- bromo
- hydrazine
- hydrazine hydrate
- ethanol
- Prior art date
Links
- NEYGWPVDXDMFOI-UHFFFAOYSA-N 4-bromo-3-(4-pentoxyphenyl)-1h-pyridazin-6-one Chemical compound C1=CC(OCCCCC)=CC=C1C1=NNC(=O)C=C1Br NEYGWPVDXDMFOI-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 12
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims abstract description 11
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- VUPLOPYKHNQUPE-UHFFFAOYSA-N methyl 3-bromo-4-oxo-4-(4-pentoxyphenyl)but-2-enoate Chemical compound CCCCCOC1=CC=C(C(=O)C(Br)=CC(=O)OC)C=C1 VUPLOPYKHNQUPE-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- -1 methyl 3-bromo-4- -oxo-4- (4-pentyloxyphenyl) -2-butenoic acid Chemical compound 0.000 abstract description 3
- 230000000507 anthelmentic effect Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 229940124339 anthelmintic agent Drugs 0.000 abstract 1
- 239000000921 anthelmintic agent Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VLYSQGRUSLORCK-UHFFFAOYSA-N 4-amino-3-(4-pentoxyphenyl)-1h-pyridazin-6-one Chemical class C1=CC(OCCCCC)=CC=C1C1=NNC(=O)C=C1N VLYSQGRUSLORCK-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Řešení se týká 5-brom-6-(4-pentyloxyfenyl)-3 (2H)-pyridazinonu vzorce I a způsobu přípravy, který spočívá v reakci metylesteru kyseliny 3-brom-4- -oxo-4-(4-pentyloxyfenyl)-2-butenové b hydrazinem nebo hydrazinhydrátem. Tato látka slouží jako meziprodukt pro přípravu anthelmintik.The present invention relates to 5-bromo-6- (4-pentyloxyphenyl) -3 (2H) -pyridazinone of formula I and the preparation method thereof in the reaction of methyl 3-bromo-4- -oxo-4- (4-pentyloxyphenyl) -2-butenoic acid b with hydrazine or hydrazine hydrate. This substance serves as an intermediate for preparation of anthelmintics.
Description
Vynález se týká 5-brom-6-(4-pentyloxyfenyl)-3(2H)-pyridazinonu vzorce IThe invention relates to 5-bromo-6- (4-pentyloxyphenyl) -3 (2H) -pyridazinone of formula I
BrBr
oc5hti (I) a způsobu jeho přípravy. OC 5 H I (I) and its preparation process.
Tato nová dosud nepopsaná látka slouží jako meziprodukt pro přípravu substituovaných 5-amino-6-(4-pentyloxyfenyl)-3(2H)-pyridazinonů s anthelmintickým účinkem čs. AO č. 255 242.This new undescribed substance serves as an intermediate for the preparation of substituted 5-amino-6- (4-pentyloxyphenyl) -3 (2H) -pyridazinones with anthelmintic effect of MS. AO No 255 242.
Sloučeninu vzorce I lze připravit reakcí podle vynálezu, jehož podstata spočívá v tom, že o sobě známý metylester kyseliny 3-brom-4-oxo-4-(4-pentyloxyfenyl)-2-butenové (Zikán V., Semonský M., Skvorová H., Kakáč B., Holubek J., Veselá H.: Collection Czechoslovak Chem. Commun. 41, 3 113 (1976)) reaguje s hydrazinem nebo hydrazinhydrátem nebo vodným roztokem hydrazinhydrátu v prostředí netečného organického rozpouštědla, výhodně alkanolu s 1 až 4 atomy uhlíku, při teplotě -10 až 40 °C, výhodně při -5 až 20 °C.The compound of the formula I can be prepared by the reaction according to the invention, characterized in that the known 3-bromo-4-oxo-4- (4-pentyloxyphenyl) -2-butenoic acid methyl ester (Zikán V., Semonský M., Skvorová) H., Kakac B., Holubek J., Vesela H .: Collection Czechoslovak Chem. Commun. 41, 3 113 (1976)) reacts with hydrazine or hydrazine hydrate or an aqueous solution of hydrazine hydrate in an inert organic solvent, preferably an alkanol having from 1 to 4 carbon atoms, at -10 to 40 ° C, preferably at -5 to 20 ° C.
Látka podle vynálezu byla připravena tak, že reagoval metylester kyseliny 3-brom-4-oxo-4-(4-pentyloxyfenyl)-2-butanové s hydrazinhydrátem nebo hydrazinem nebo vodným roztokem hydrazinhydrátu při teplotě -5 až 5 °C v etanolu, načež se teplota reakční směsi nechala stoupnout na 20 °C. Při použití hydrazinu nebo hydrazinhydrátu bylo získáno přes 90 % teorie látky vzorce I o vyhovující čistotě; při použiti vodného roztoku hydrazinhydrátu byl výtěžek nižší.The compound of the invention was prepared by reacting 3-bromo-4-oxo-4- (4-pentyloxyphenyl) -2-butanoic acid methyl ester with hydrazine hydrate or hydrazine or an aqueous solution of hydrazine hydrate at -5 to 5 ° C in ethanol, whereupon the temperature of the reaction mixture was allowed to rise to 20 ° C. Using hydrazine or hydrazine hydrate, over 90% of the theory of a compound of formula I of satisfactory purity was obtained; when using an aqueous solution of hydrazine hydrate, the yield was lower.
Bližší podrobnosti plynou z následujících příkladů provedení, které vynález pouze ilustrují, nikoliv omezují.The following examples illustrate the invention but do not limit it.
Příklad 1Example 1
K roztoku 6,4 g (186 mmol) 93% hydrazinu v 80 ml etanolu se za míchání přikape roztok 35,5 g (100 mmol) metylesteru kyseliny 3-brom-4-oxo-4-(4-pentyloxyfenyl)-2-butenové v 80 ml etanolu při teplotě 1 až 5 °C a suspenze se míchá po dobu 1 h při teplotě místnosti. Odsátím reakční směsi a zpracováním matečných louhů po odsátí se získá celkem 32,28 g (96 %) produktu, který po krystalizaci z etanolu poskytne látku o t.t. 198 až 199 °C a složeníTo a solution of 6.4 g (186 mmol) of 93% hydrazine in 80 mL of ethanol was added dropwise a solution of 35.5 g (100 mmol) of methyl 3-bromo-4-oxo-4- (4-pentyloxyphenyl) -2- butene in 80 ml of ethanol at 1 to 5 ° C and the suspension is stirred for 1 h at room temperature. A total of 32.28 g (96%) of product is obtained by suctioning off the reaction mixture and treating the mother liquors after suction. 198 DEG-199 DEG C. and composition
Příklad 2Example 2
K roztoku 42 g (0,839 mol) 100% hydrazinhydrátu v 500 ml etanolu se za míchání přidá roztok 231 g (0,650 mol) metylesteru kyseliny 3-brom-4-oxo-4-(4-pentyloxyfenyl)-2-butenové v 500 ml etanolu tak, aby teplota reakčni směsi byla v rozmezí -10 až -6 °C. Směs se dále míchá po dobu 1 h při teplotě -6 až -3 °C a pak ještě 1 h při teplotě místnosti. Zpracováním uvedeným v příkladu 1 se získá 199,1 g (91 %) produktu, který po krystalizaci z etanolu taje při 198,2 až 199,4 °C.To a solution of 42 g (0.839 mol) of 100% hydrazine hydrate in 500 ml of ethanol is added with stirring a solution of 231 g (0.650 mol) of methyl 3-bromo-4-oxo-4- (4-pentyloxyphenyl) -2-butenoate in 500 ml. ethanol so that the temperature of the reaction mixture is between -10 and -6 ° C. The mixture was further stirred for 1 h at -6 to -3 ° C and then for 1 h at room temperature. The work-up described in Example 1 afforded 199.1 g (91%) of product which melts at 198.2-199.4 ° C after crystallization from ethanol.
Příklad 3Example 3
K roztoku 12 g (0,192 mol) 80% vodného hydrazinhydrátu ve 100 ml etanolu se přikape roztok 53,25 g (0,15 mol) metylesteru kyseliny 3-brom-4-oxo-4-(4-pentyloxyfenyl)-2-butenové ve 120 ml etanolu při teplotě -2 až 0 °C. Suspenze se míchá 1 h při teplotě 0 °C a pak 1 h při teplotě místnosti. Zpracováním podle příkladu 1 se získá 38 g (75 %) produktu, který po krystalizaci Z etanolu taje při 198,3 až 199 °C.To a solution of 12 g (0.192 mol) of 80% aqueous hydrazine hydrate in 100 ml of ethanol is added dropwise a solution of 53.25 g (0.15 mol) of 3-bromo-4-oxo-4- (4-pentyloxyphenyl) -2-butenoic acid methyl ester. in 120 ml of ethanol at a temperature of -2 to 0 ° C. The suspension was stirred at 0 ° C for 1 h and then at room temperature for 1 h. Working up according to Example 1 gives 38 g (75%) of a product which melts at 198.3-199 ° C after crystallization from ethanol.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS867564A CS255243B1 (en) | 1986-10-18 | 1986-10-18 | 5-brom-6-(4-pentyloxyphenyl)-3-(2h)pyridazinon and process for preparing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS867564A CS255243B1 (en) | 1986-10-18 | 1986-10-18 | 5-brom-6-(4-pentyloxyphenyl)-3-(2h)pyridazinon and process for preparing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS756486A1 CS756486A1 (en) | 1987-06-11 |
| CS255243B1 true CS255243B1 (en) | 1988-02-15 |
Family
ID=5425023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS867564A CS255243B1 (en) | 1986-10-18 | 1986-10-18 | 5-brom-6-(4-pentyloxyphenyl)-3-(2h)pyridazinon and process for preparing the same |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS255243B1 (en) |
-
1986
- 1986-10-18 CS CS867564A patent/CS255243B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS756486A1 (en) | 1987-06-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1101760B1 (en) | Difluoromethanesulfonyl anilide derivatives, process for the preparation of them and herbicides containing them as the active ingredient | |
| JPS6155514B2 (en) | ||
| EP0096297B1 (en) | Process for the preparation of 1-sulfo-2-oxoazetidine derivatives | |
| DE69327890T2 (en) | Process for the preparation of 2- (un) substituted 4-alkylimidazoles | |
| IL29887A (en) | N-substituted-2,4,5-trihalo imidazole derivatives,their preparation,and their use as acaricides | |
| EP0045910B1 (en) | Indole derivatives and process for their production | |
| US3997533A (en) | Process for the preparation of 7-acylamino-desacetoxycephalosporanic derivatives | |
| US4217450A (en) | Imidazoledicarboxylic acid substituted cephalosporin derivatives | |
| DE69401182T2 (en) | Process for the preparation of a benzothiadiazole derivative | |
| HU191515B (en) | Process for the preparation of thioethers | |
| CS255243B1 (en) | 5-brom-6-(4-pentyloxyphenyl)-3-(2h)pyridazinon and process for preparing the same | |
| EP0258182A1 (en) | Semicarbazones and thiosemicarbazones | |
| Bosin et al. | Routes of functionalized guanidines. Synthesis of guanidino diesters | |
| US4035378A (en) | Process for the production of 1,3,4-thiadiazol-5(4H)-onyl dithiophosphoric acid esters | |
| US4808752A (en) | Process for the preparation of 2-aminophenyl thioethers | |
| US4711959A (en) | 2-cyanoamino-pyrimidines | |
| US4033960A (en) | 2-Mercaptoquinoxaline-di-N-oxide products and a method for their preparation | |
| EP0015631B1 (en) | ((4,5-dihydro-5-thioxo-1h-1,2,4-triazol-3-yl)thio)acetic acid and its salts | |
| EP0293742A1 (en) | Process for the production of 4-nitro-5-imidazolylethers and -thioethers | |
| US4659820A (en) | Process for the preparation of 4-alkoxy-6-alkyl-2-cyanamino-1,3,5-triazines | |
| JPS5910351B2 (en) | Method for producing 3-oxy-1,2,4-triazole derivative | |
| EP0359474B1 (en) | Pyridazinone manufacture | |
| US3494921A (en) | 1,4-disubstituted pyridazino(4,5-d) pyridazines | |
| EP0115323A2 (en) | Process for producing heterocyclic compound having nitromethylene group as the side chain group | |
| SU799660A3 (en) | Method of preparing 5/6-(cyclopropylethyl)-sulfinyl/-benzimidazole-2-methylcarbamate |