CS235153B1 - 2-(substituted)-4,5-dichlor-3-oxo-2h-pyridazines - Google Patents
2-(substituted)-4,5-dichlor-3-oxo-2h-pyridazines Download PDFInfo
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- CS235153B1 CS235153B1 CS147383A CS147383A CS235153B1 CS 235153 B1 CS235153 B1 CS 235153B1 CS 147383 A CS147383 A CS 147383A CS 147383 A CS147383 A CS 147383A CS 235153 B1 CS235153 B1 CS 235153B1
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- pyridazines
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- -1 2-(substituted)-4,5-dichlor-3-oxo-2h-pyridazines Chemical class 0.000 title claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- VBEUIQSKUWJLSL-UHFFFAOYSA-N 4,5-dichloro-2-(chloromethyl)pyridazin-3-one Chemical compound ClCN1N=CC(Cl)=C(Cl)C1=O VBEUIQSKUWJLSL-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Chemical group 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001356 alkyl thiols Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000011591 potassium Chemical group 0.000 claims description 2
- 229910052700 potassium Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- WPQWITCZLCIZNZ-UHFFFAOYSA-N sodium;2,4,5-trichlorophenol Chemical compound [Na].OC1=CC(Cl)=C(Cl)C=C1Cl WPQWITCZLCIZNZ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Plural Heterocyclic Compounds (AREA)
Description
Vynález sa týká 2-(substituovaných )-4,5-dichlór-3-oxo-2H-pyridazínov ako aj sposobu ich přípravy. Uvedené zlúčeniny sa móžu použit ako východiskové produkty k syntéze pesticidně účinných látok, ako napr. na přípravu 2-substituovaných-4-alkoxy (alkyltio )-5-chlór-3-oxo-2H-pyridazínov, 2-suhstituovaných-4-chlór-5-alkoxy (alkyltio j-3-oxo-2H-pyridazínov.The invention relates to 2- (substituted) -4,5-dichloro-3-oxo-2H-pyridazines as well as a process for their preparation. Said compounds can be used as starting products for the synthesis of pesticidally active substances, such as e.g. for the preparation of 2-substituted-4-alkoxy (alkylthio) -5-chloro-3-oxo-2H-pyridazines, 2-substituted-4-chloro-5-alkoxy (alkylthio) -3-oxo-2H-pyridazines.
Z literatúry sú známe 2-dialkylaminoetyl(-4,5-dichlór-3-oxo-2H-pyridazíny, 2-rodonometyl-4,5-dichlór-3-oxo-2H-pyridazíny ako i 2-hydroxymetyl (chlórmetyl) -4,5-dichlór-3-oxo-2H-pyridazíny ako východiskové látky k syntéze početných zlúčenín [Monatsheffte fur Chemie 99, 15—04 (1968)].2-dialkylaminoethyl (-4,5-dichloro-3-oxo-2H-pyridazines, 2-rhodonomethyl-4,5-dichloro-3-oxo-2H-pyridazines as well as 2-hydroxymethyl (chloromethyl) -4 are known from the literature. 5-dichloro-3-oxo-2H-pyridazines as starting materials for the synthesis of numerous compounds [Monatsheffte fur Chemie 99, 15-04 (1968)].
Teraz boli nájdené 2-(substituované )-4,5-dichlór-3-oxo-2H-pyridazíny všeobecného2- (substituted) -4,5-dichloro-3-oxo-2H-pyridazines in general have now been found
v ktorom R znamená alkyl s 1 až 4 atómami uhlíka, fenyl, připadne substituovaný 1 až 3 substituentami vybratými zo skupiny zahrnujúcej metylskupinu, halogén, nitroskupinu, trifluormetylskupinu a X znamená kyslík alebo síru.wherein R is C 1 -C 4 alkyl, phenyl optionally substituted with 1 to 3 substituents selected from the group consisting of methyl, halogen, nitro, trifluoromethyl, and X is oxygen or sulfur.
Súčasne bol zistený sposob přípravy zlúčenín všeobecného vzorce I, reakciou 2-chlórmetyl-4,5-dichlór-3-oxo-2H-pyridazínu vzórca II,At the same time, a process for the preparation of compounds of the formula I by reacting 2-chloromethyl-4,5-dichloro-3-oxo-2H-pyridazine of formula II,
Cl xy 0 lili s alkoholom, alkyltiolom, fenolom alebo tíofenolom vš. vzórca IIICl xy 0 with alcohol, alkylthiol, phenol or thiophenol, all; vzórca III
MX-R (III) v ktorom R, X majú už uvedený význam a M znamená vodík, sodík alebo draslík v prostředí organického rozpúšťadla ako je metylalkohol, etylalkohol, aceton, butylester kyseliny octovej, benzén, toluén a pod. pri teplote —15 až -j-60 °C. V případe, ak M znamená vodík, reakcia sa uskutočňuje aj za přítomnosti terč. aminu ako je pyridin, trimetylamín, trietylamín, N,N-dimetylanilín a podobné.MX-R (III) wherein R, X are as defined above and M is hydrogen, sodium or potassium in an organic solvent such as methanol, ethanol, acetone, butyl acetate, benzene, toluene and the like. at a temperature of from -15 ° C to -60 ° C. In the case where M is hydrogen, the reaction is also carried out in the presence of a target. amines such as pyridine, trimethylamine, triethylamine, N, N-dimethylaniline and the like.
Nasledujúce příklady osvetlujú, ale neobmedzujú predmet vynálezu.The following examples illustrate but do not limit the scope of the invention.
Příklad 1Example 1
2-metoxymetyl-4,5-dichlór-3-oxo-2-H-pyridazín2-methoxymethyl-4,5-dichloro-3-oxo-2-H-pyridazin
K 0,2 molu 2-chlórmetyl-4,5-dichlór-3-oxo-2H-pyridazínu v 200 ml metylalkoholu sa pri teplote 0 až 5 °C za miešania postupné přidalo 0,21 molu metylátu sodného v 80 mililitroch metylalkoholu. Potom sa reakčná zmes miešala pri teplote miestnosti 30 min. a dalších 30 min. pri teplote 50 °C. Po 0chladnutí sa vylúčený chlorid sodný oddělil filtráciou, z filtrátu sa za zníženého tlaku oddestiloval metylalkohol. Destilačný zvyšok sa rozpustil v 200 ml toluénu, premyl sa 200 ml vody, vysušil, toluén sa oddestiloval za zníženého tlaku a zbytok sa přečistil kryštalizáciou. Získala sa biela kryštalická látka s t. t. 115—117 °C v 70, 1%-nom výtažku, nasledujúceho zloženia:To 0.2 mol of 2-chloromethyl-4,5-dichloro-3-oxo-2H-pyridazine in 200 ml of methanol at 0-5 ° C was added successively 0.21 mol of sodium methylate in 80 ml of methanol. Then the reaction mixture was stirred at room temperature for 30 min. and another 30 min. at 50 ° C. After cooling, the precipitated sodium chloride was removed by filtration, and methanol was distilled off under reduced pressure. The distillation residue was dissolved in 200 ml of toluene, washed with 200 ml of water, dried, toluene was distilled off under reduced pressure and the residue was purified by crystallization. A white crystalline substance with m.p. t. 115 DEG -117 DEG C. in 70.1% yield, having the following composition:
Analýza-pre C&HeClzNžOa (m. h. 209,0):Analysis for C & HeCl2N2Oa (MW 209.0):
Vypočítané:calculated:
13,40 % N, 33,92 % Cl Nájdené:13.40% N, 33.92% Cl Found:
13,29 '% N, 34,17 % Cl IC v CCU:13.29% N, 34.17% Cl IC in CCU:
v(C = O), 1688 cm-1 v(C = N), 1612 cm1 v (C = O), 1688 cm -1 v (C = N), 1612 cm -1
UV v CH3OH:UV in CH3OH:
^max (nm) (log ε) 216,0 (4,53)max max (nm) (log ε) 216.0 (4.53)
297,4 (3,80)297.4 (3.80)
Příklad 2Example 2
2-etoxometyl-4,5-dichlór-3-oxo-2H-pyridazín2-etoxometyl-4,5-dichloro-3-oxo-2H-pyridazin
K 0,2 mólu 2-chlórmetyl-4,5-dichlór-3-oxo-2H-pyridazínu v 200 ml etylalkoholu sa za miešania postupné přidalo 0,21 mólu etylátu sodného a 100 ml etylalkoholu pri teplote 5 až 10 °C. Další postup bol rovnaký ako v příklade 1. Získala sa biela kryštalická látka s t. t. 101—102 °C, v 90,5 %-nom výtažku, nasledujúceho zloženia:To 0.2 mole of 2-chloromethyl-4,5-dichloro-3-oxo-2H-pyridazine in 200 ml of ethyl alcohol was added, with stirring, 0.21 mole of sodium ethylate and 100 ml of ethyl alcohol at 5-10 ° C. The further procedure was the same as in Example 1. A white crystalline substance with m.p. t. 101-102 ° C, in 90.5% yield, having the following composition:
Analýza pre C7H8CI2N2O2 (m. h. 223,0)Analysis for C7H8Cl2N2O2 (m, h, 223.0)
Vypočítané:calculated:
12,56 % N, 31,79 % Cl Nájdené:12.56% N, 31.79% Cl Found:
12,88 % N, 31,99 % ClN, 12.88. Cl, 31.99
IC v CC14:IC in CC14:
v(C = C), 1686 cm-1 v(C = C), 1609 cm-1 v CHCb:v (C = C), 1686 cm -1 v (C = C), 1609 cm -1 in CHCl 3:
v(C = C), 1674 cm1 v(C —N), 1611 cm-1 v (C = C), 1674 cm -1 v (C = N), 1611 cm -1
UV v CHsOH:UV in CH 2 OH:
λ max nm (log ε) 215,9 (4,52) 296,4 (4,33)λ max nm (log ε) 215.9 (4.52) 296.4 (4.33)
Příklad 3Example 3
2-etyltiometyl-4,5-dichlór-3-oxo-2H-pyridazín2-ethylthiomethyl-4,5-dichloro-3-oxo-2H-pyridazin
K 0,206 mólu 2-chlórmetyl-4,5-dichlór-3-oxo-2H-pyridazínu v 150 ml acetonitrilu sa za miešania pri teplote 0 až 5 °C přidalo 0,206 molu etylmerkaptidu sodného suspendovaného v 100 ml benzénu. Po přidaní sa v miešaní pokračovalo 1 h. pri 20 °C a 30 min. pri 55 °C. Vylúčený chlorid sodný sa oddělil filtráciou, z filtrátu sa za zníženého tlaku oddestiloval acetonitril a benzén. Další postup je rovnaký ako v příklade 1. Získala sa biela kryštalická látka s t. t. 94 až 96 °C v 81 %-nom výťažku, nasledujúceho zloženia:To 0.206 mol of 2-chloromethyl-4,5-dichloro-3-oxo-2H-pyridazine in 150 ml of acetonitrile was added 0.206 mol of ethyl mercaptide sodium suspended in 100 ml of benzene with stirring at 0-5 ° C. After the addition, stirring was continued for 1 h. at 20 ° C and 30 min. at 55 ° C. The precipitated sodium chloride was removed by filtration, and acetonitrile and benzene were distilled off under reduced pressure. The further procedure is the same as in Example 1. A white crystalline substance with m.p. t. 94 DEG-96 DEG C. in 81% yield, as follows:
C7H8CI2N2OS (m. h. 239,1):C7H8Cl2N2OS (m, d, 239.1):
Vypočítané:calculated:
11,71 % N, 29,65 % Cl, 13,41 '% SN, 11.71; Cl, 29.65; S, 13.41%
Nájdené:found:
12,01 % N, 29,73 % Cl, 13,50 % SN, 12.01; Cl, 29.73; S, 13.50
IC spektra v CCI4: v(C = O), 1684 cm-1 v(C = N), 1589 cm-1 IC spectra in CCl4: v (C = O), 1684 cm -1 v (C = N), 1589 cm -1
UK spektrá v CH3OH:UK spectra in CH3OH:
Amax (nm) (log ε) 213,4 (4,25)A max (nm) (log ε) 213.4 (4.25)
305,0 (4,09)305.0 (4.09)
Příklad 4Example 4
2i(4‘-di'Chlóirf0nyltiometyl)-4,5-dichlór-3-oxo-2H-pyridazín2 R (4'-di'Chlóirf0nyltiometyl) -4,5-dichloro-3-oxo-2H-pyridazin
K 0,2 mólu 2-chlórmetyl-4,5-dichlór-3-oxo-2H-pyridazínu v 150 ml acetonitrilu sa za miešania prí 4 až 10 °C postupné přidalo 0,2 mólu sodnej soli 4-chlórtiofenolátu sodného. V miešaní sa pokračovalo 1 h. pri laboratórnej teplote a 30 min. pri 40 °C. Další postup bol rovnaký, ako v příkladu 1. Získala sa žitá viskózna kvapalina v 75 %-nom výťažku, nasledujúceho zloženia:To 0.2 mol of 2-chloromethyl-4,5-dichloro-3-oxo-2H-pyridazine in 150 ml of acetonitrile was added 0.2 mol of sodium 4-chlorothiophenolate sodium gradually with stirring at 4-10 ° C. Stirring was continued for 1 h. at room temperature and 30 min. at 40 ° C. The further procedure was the same as in Example 1. A viscous viscous liquid was obtained in 75% yield, having the following composition:
C11H7CI2N2OS (m. h. 321,6):C11H7Cl2N2OS (m, d, 321.6):
Vypočítané:calculated:
8,71 % N, 33,11 % Cl, 9,97 % SN, 8.71; Cl, 33.11; S, 9.97
Nájdené:found:
8,91 % N, 33,40 % Cl, 10,11 % S Příklad 5N 8.91, Cl 33.40, S 10.11. Example 5
2‘-(2‘,4‘,5‘-trichlórf enoxymetyl)-4,5-dichlór-3-oxo-2H-pyridazín2‘- (2‘, 4‘, 5‘-trichlorophenoxymethyl) -4,5-dichloro-3-oxo-2H-pyridazine
K 0,15 molu 2-chlórmetyl-4,5-dichlór-3-oxo-2H-pyridazínu v 100 ml metyletylketónu za miešania sa přidalo 0,15 mólu sodnej soli 2,4,5-trichlórfenolu v 50 ml metyletylketónu, pri teplote 20 °C. V miešaní sa pokračovalo 30 min. pri laboratórnej teplote a 1 h. pri 75 °C. Ďalší postup bol rovnaký ako v příklade 1. Získala sa biela krystalická látka (z metylalkoholu) s t. t. 152 až 154 °C, nasledujúceho zloženia:To 0.15 mol of 2-chloromethyl-4,5-dichloro-3-oxo-2H-pyridazine in 100 ml of methyl ethyl ketone with stirring was added 0.15 mol of 2,4,5-trichlorophenol sodium in 50 ml of methyl ethyl ketone, at a temperature of Deň: 18 ° C. Stirring was continued for 30 min. at room temperature and 1 h. at 75 ° C. The further procedure was the same as in Example 1. A white crystalline substance (from methanol) with m.p. t. 152-154 ° C, having the following composition:
C11H5CI5N2O2 (m. h. 374,41):C11H5Cl5N2O2 (m, h 374.41):
Vypočítané:calculated:
7,48 % N, 47,30 % ClN, 7.48; Cl, 47.30
Nájdené:found:
7,52 % N, 47,23 % ClN, 7.52; Cl, 47.23
Rovnakým postupom boli připravené následovně látky:The following substances were prepared in the same manner:
2- (4‘-brómf enoxymetyl j -4,5-dichlór-3-oxo-2H-pyridazín, t. t. 161—163 °C,2- (4‘-bromophenoxymethyl) -4,5-dichloro-3-oxo-2H-pyridazine, mp 161-163 ° C,
2- (4‘-f luórf enoxymetyl j -4,5-dichlór-3-oxo-2H-pyridazín, t. t. 91—93 °C,2- (4‘-fluorophenoxymethyl) -4,5-dichloro-3-oxo-2H-pyridazine, mp 91-93 ° C,
2- (m-tolyloxymetyl) -4,5-dichlár-3-oxo-2H-pyridazín, t. t. 70—72 °C,2- (m-tolyloxymethyl) -4,5-dichloro-3-oxo-2H-pyridazine, m.p. t. 70 - 72 ° C,
2- (4‘-nitrof enoxymetyl j -4,5-dichlór-3-oxo-2H-pyridazín, t. t. 184—187 °C,2- (4‘-nitrophenoxymethyl) -4,5-dichloro-3-oxo-2H-pyridazine, mp 184-187 ° C,
2- (4‘-trif luormetylf enoxymetyl j -4,5-dichlór-3-oxo-2H-pyridazín, t. t. 61—63 °C.2- (4‘-Trifluoromethylphenoxymethyl) -4,5-dichloro-3-oxo-2H-pyridazine, mp 61-63 ° C.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS147383A CS235153B1 (en) | 1983-03-03 | 1983-03-03 | 2-(substituted)-4,5-dichlor-3-oxo-2h-pyridazines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS147383A CS235153B1 (en) | 1983-03-03 | 1983-03-03 | 2-(substituted)-4,5-dichlor-3-oxo-2h-pyridazines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS235153B1 true CS235153B1 (en) | 1985-05-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS147383A CS235153B1 (en) | 1983-03-03 | 1983-03-03 | 2-(substituted)-4,5-dichlor-3-oxo-2h-pyridazines |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS235153B1 (en) |
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1983
- 1983-03-03 CS CS147383A patent/CS235153B1/en unknown
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