CS252899B1 - Method of glyoxal bis phenylhydrazones preparation - Google Patents
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Abstract
Postup rieši sposob přípravy bis(2,4-dinitrofenylhydrazón[glyoxalu, bis(4-nitrofenylhydrazón[glyoxalu a bis(2,3-dichlórfenylhydrazón [glyoxalu. Uvedeného účelu sa dosiahne tým, že glyoxal, získaný oxidáciou etylémglykolu, resp. jeho oligomérov, s výhodou dietylénglykol, trietylénglyikol atď. pri teplote 160 až 190 °C s dvojchromanom draselným a kyselinou sírovou v molárnych poměrech 1: 4, sa působením 2,4-dinítrofenylhydrazínu, 4-nitrofenylhydrazínu a 2,5- -dichlórfenylhydrazmu prevedie na vyššie uvedené hydrazóiny. Uplatnenie v Iklinickom, resp. veterinárnom výskume a praxi v důsledku vysokej antimikrobiálnej účinnosti připravených hydrazónov.The process is solved by a process for preparing bis (2,4-dinitrophenylhydrazone [glyoxal, bis (4-nitrophenylhydrazone [glyoxal and bis (2,3-dichlorophenylhydrazone) [glyoxal. That purpose is achieved by glyoxal obtained by oxidation ethyl glycol, respectively. its oligomers, preferably diethylene glycol, triethylene glycol, and the like. at 160-190 ° C with dichromate potassium and sulfuric acid in molar ratios of 1: 4, with 2,4-dinitrophenylhydrazine, 4-nitrophenylhydrazine and 2,5- -dichlorophenylhydrazine is converted to above of said hydrazolines. Application in Iclinic, resp. veterinary research and practice as a result high antimicrobial efficacy hydrazones prepared.
Description
Vynález sa týká přípravy his fenylihydrazónov glyoxalu.The invention relates to the preparation of his phenylihydrazones of glyoxal.
Z literatury [J. Zemeik a spol., Folia Microb.Ol. 22, 237 (1977); 23, 304 (1978); 30, 396 (1985)] je známe, že hydrazóny, resp. osazóny .niektorých aldehydov a ketónov vykazujú antimikrobiálnu účinnost. Z doteraz v literatúre popísaných postupov přípravy glyoxalu najvýlhodnejší je postup založený na oxídácii acetaldehydu s kysličníkom seleničitým, resp. kyselinou seleničitou, pričom glyoxal sa získá s 18 % výtažku [A. R. Ronzio, T. D. Wangh, Org. Syntih. Coll. Vol. 3, 438 (1955)].From Literature [J. Zemeik et al., Folia Microb.Ol. 22, 237 (1977); 23, 304 (1978); 30, 396 (1985)], it is known that hydrazones, respectively. the osazones of some aldehydes and ketones show antimicrobial activity. Of the processes described in the literature to date for the preparation of glyoxal, the most preferred is the process based on oxidation of acetaldehyde with selenium oxide, respectively. selenic acid, the glyoxal being obtained in 18% yield [A. R. Ronzio, T. D. Wangh, Org. Syntih. Coll. Vol. 3, 438 (1955)].
Podstata vynálezu spočívá v tom, že sa na etyléngiykol alebo jeho oligoméry ako· je dietyíenglykol, trietylénglykol působí 1 až 3 h oxidačnou zmesou dvojchromanu draselného· a kyseliny sírovej v molárnych poměrech 1: 4. Oxidáciou vzniknutý glyoxal (výťažok 3 až 4 % j sa z reakčnej zmesi oddestiluje a v ďalšom stupni působením derivátov fenylhydrazínu sa získajú jeho bis fenylhydrazóny.SUMMARY OF THE INVENTION Ethylene glycol or its oligomers such as diethylene glycol, triethylene glycol are treated for 1 to 3 hours with an oxidation mixture of potassium dichromate and sulfuric acid in molar ratios of 1: 4. it is distilled off from the reaction mixture and subsequently treated with phenylhydrazine derivatives to give its bis phenylhydrazones.
Výhodou navrhovaného spůsoibu je jeho jednoduchost prevedenia a ihlavne inižšie ekonomické náklady použitých chemikálií (cca 10-krát menšie] oproti přípravě popísanej (Ronzio a spol. j.The advantage of the proposed method is its ease of execution and the costly economic cost of the chemicals used (about 10 times less) than the preparation described (Ronzio et al.
Příklad 1Example 1
Do 500 ml trojhrdlej banky opatrenej spatným chladičem, na fctorom je umiestnený destilačný chladič s prikvapkávajúcim lieviikom sa dá 10,5 g etylénglylkolu. Zmes 32 g dvojchromanu 'draselného a 24 ml kyseliny sírovej v 200 ml vody sa postupné v priebehu 2 hodin přidává, pričom teplota reakčnej zmesi sa udržuje pri 160 až 170 °C. Vznikej úce oxidačně produkty destilujú spolu s vodou, pričom sa získá cca 40 ml roztoku. K tomuto roztoku sa pridajú 3 g 2,4-dinitrofenylhydrazínu v 40 ml etanolu a zmes sa refluxuje 2 hod. Po ochladení roztoku sa zísfca 2,62 g (3,7 °/o) oranžovožltých kryštálov ibis (2,4-dinitrofenylhydrazón (glyoxalu o t. t. = 158 až 160 °C. Kryštalizáciou z metanolu sa získá analytická vzorka o t. t. = = 160 až 161 C'C.10.5 g of ethylene glycol are placed in a 500 ml three-necked flask equipped with an inverted condenser and a distillation condenser is added to the dropping funnel. A mixture of 32 g of potassium dichromate and 24 ml of sulfuric acid in 200 ml of water is added gradually over 2 hours while maintaining the temperature of the reaction mixture at 160-170 ° C. The resulting oxidation products are distilled together with water to obtain about 40 ml of solution. To this solution was added 3 g of 2,4-dinitrophenylhydrazine in 40 ml of ethanol and the mixture was refluxed for 2 hours. After cooling the solution, 2.62 g (3.7%) of orange-yellow ibis crystals (2,4-dinitrophenylhydrazone (glyoxal, mp = 158-160 ° C) were obtained. Crystallization from methanol gave an analytical sample of mp = 160-160 ° C. 161 ° C
Analýza počítaná pre CuHioOsNs: C 40,22, H 2,41, N 26,85. Nájdené: C 40,41, H 2,88, N 26,96.Calcd for C 10 H 10 O 5 N 5: C 40.22, H 2.41, N 26.85. Found: C 40.41, H 2.88, N 26.96.
Příklad 2Example 2
Postupuje sa ako v příklade 1 s tým rozdielom, že namiesto 2,4-dinitrofenýlhydrazí•nu sa použije 4-nitrofenylhydrazín. Získá sa 1,94 (3,5 %) bis(4-nitrofenylhydrazónjglyoxalu o t. t. = 140 °C.The procedure was as in Example 1 except that 4-nitrophenylhydrazine was used instead of 2,4-dinitrophenylhydrazine. 1.94 (3.5%) of bis (4-nitrophenylhydrazone) glyoxal is obtained, m.p. = 140 ° C.
Analýza počítaná pre C14H12O4N6: C 51,21, H 3,70, N 25,62. Nájdené: C 51,38, H 3,62, N 25,84.Analysis calculated for C 14 H 12 O 4 N 6: C 51.21, H 3.70, N 25.62. Found: C, 51.38; H, 3.62; N, 25.84.
Příklad 3Example 3
Postupuje sa ako· v přiklade 1 s tým rozdielom, že namiesto 2,4-dinltrofenylhydrazínu sa použije 2,5-dichlórfenylihydrazín. Získá sa 1,48 g (2,4 %) bis (2,5-dichlorfenylhydrazón) glyoxalu o t. t. = 225 °C.The procedure is as in Example 1, except that 2,5-dichlorophenyllirazine is used instead of 2,4-dintrophenylhydrazine. 1.48 g (2.4%) of bis (2,5-dichlorophenylhydrazone) glyoxal, m.p. t. Melting point = 225 DEG.
Analýza počítaná pre C14H10N4CI4: C 44,70, H 2,66, N 14,90, Cl 37,73. Nájdené: C 44,83, H 2,71, N 14,75, Cl 37,90. .For C14H10N4Cl4: C, 44.70; H, 2.66; N, 14.90; Cl, 37.73. Found: C 44.83, H 2.71, N 14.75, Cl 37.90. .
Příklad 4Example 4
Postupuje sa ako v příklade 1 s tým ro.zdielom, že namiesto etylénglylkolu sa použije na oxidáciu trietylénglykol a reakčná teplota sa udržuje v Intervale 180 až 190 °C počas 3 hodin. Získá sa 0,9 g (3,1 %) bis(2,4-dinitrofenylhydrazón jglyogalu o t. t. = = 160 až 161 °C.The procedure is as in Example 1, except that instead of ethylene glycol, triethylene glycol is used for the oxidation and the reaction temperature is maintained at an interval of 180-190 ° C for 3 hours. 0.9 g (3.1%) of bis (2,4-dinitrophenylhydrazone) -glyogal is obtained, m.p. = 160-161 ° C.
V důsledku vysokej antimikrobiálnej účinnosti fenylhydrazónov glyoxalu, rádovo váčšej oproti doteraz známým hydrazónom, vynález může nájsť uplatnenie v medicinálnom, veterinárnom, připadne farmaceutickom výskume a praxi.Due to the high antimicrobial activity of phenylhydrazones of glyoxal, of an order of magnitude greater than the previously known hydrazones, the invention can find application in medical, veterinary, or pharmaceutical research and practice.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS861739A CS252899B1 (en) | 1986-03-13 | 1986-03-13 | Method of glyoxal bis phenylhydrazones preparation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS861739A CS252899B1 (en) | 1986-03-13 | 1986-03-13 | Method of glyoxal bis phenylhydrazones preparation |
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| CS173986A1 CS173986A1 (en) | 1987-02-12 |
| CS252899B1 true CS252899B1 (en) | 1987-10-15 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS861739A CS252899B1 (en) | 1986-03-13 | 1986-03-13 | Method of glyoxal bis phenylhydrazones preparation |
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| CS173986A1 (en) | 1987-02-12 |
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