CS243441B1 - Hydrogen sulphates of alkaline metals' acryl 3-aminobenzoates and method of their production - Google Patents
Hydrogen sulphates of alkaline metals' acryl 3-aminobenzoates and method of their production Download PDFInfo
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- CS243441B1 CS243441B1 CS8410646A CS1064684A CS243441B1 CS 243441 B1 CS243441 B1 CS 243441B1 CS 8410646 A CS8410646 A CS 8410646A CS 1064684 A CS1064684 A CS 1064684A CS 243441 B1 CS243441 B1 CS 243441B1
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- alkyl
- potassium
- sodium
- formula
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- 238000000034 method Methods 0.000 title claims description 6
- -1 acryl 3-aminobenzoates Chemical class 0.000 title abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title description 2
- 229910052751 metal Inorganic materials 0.000 title 1
- 239000002184 metal Substances 0.000 title 1
- 150000002739 metals Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 239000011734 sodium Substances 0.000 claims abstract description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 abstract description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 7
- 239000011591 potassium Substances 0.000 claims abstract description 7
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims 1
- 239000001120 potassium sulphate Substances 0.000 claims 1
- 238000005185 salting out Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 241000251539 Vertebrata <Metazoa> Species 0.000 abstract description 4
- 206010002091 Anaesthesia Diseases 0.000 abstract description 2
- 230000037005 anaesthesia Effects 0.000 abstract description 2
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- UBBSASFKEJHWOE-UHFFFAOYSA-M potassium hydrogen sulfate sulfuric acid Chemical compound [K+].OS(O)(=O)=O.OS([O-])(=O)=O UBBSASFKEJHWOE-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PANBYUAFMMOFOV-UHFFFAOYSA-N sodium;sulfuric acid Chemical compound [Na].OS(O)(=O)=O PANBYUAFMMOFOV-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Hydrogenaulfáty alkyl 3-aninobeasoátů alkalických kovů obecněho vsorca X, kdo R snačl alkyl a 1 ai 3 stony uhlíku a M snačí sodík nebo draslík, jsou vhodná k anestesi poikilotsrnníeh obratlovců. Jejich výroba spočívá v ton, is as as alkyl 3-sninobensoát obecného vzorce XX. kde R ná shora uvedený výsnaa, působí skvivalsntnín aaoistvínhydrogensulfátu sodného nebo draselného v polární· rospouitědle nísitslaén · vodou, popřípadi jejich sněaí, při teplotě 20 ai 80 C, načet se vyloučený produkt obecného vsorca X odsaje.Alkyl 3-aninobeasoate hydrogen sulfates alkali metals generally X, who R labeled alkyl and 1 to 3 carbon atoms and M down sodium or potassium, are suitable for anesthesia poikilotsrnníeh vertebrates. Their production consists of tons, is as and alkyl 3-sninobensoate of formula XX. where R is from above said seed, acts as a squaline and avaine hydrogen sulfate sodium or potassium in the polar rospouitědle nísitslaén · by water in case of snow, at temperature 20 and 80 C, load the excluded product X-ray suck.
Description
(54) Hydrogensulfáty alkyl 3-aminobenzoátů alkalických kovů a způsob jejich výroby(54) Alkali metal alkyl 3-aminobenzoates hydrogen sulphates and process for their preparation
Hydrogenaulfáty alkyl 3-aninobeasoátů alkalických kovů obecněho vsorca X, kdo R snačl alkyl a 1 ai 3 stony uhlíku a M snačí sodík nebo draslík, jsou vhodná k anestesi poikilotsrnníeh obratlovců. Jejich výroba spočívá v ton, is as as alkyl 3-sninobensoát obecného vzorce XX. kde R ná shora uvedený výsnaa, působí skvivalsntnín aaoistvínhydrogensulfátu sodného nebo draselného v polární· rospouitědle nísitslaén · vodou, popřípadi jejich sněaí, při teplotě 20 ai 80 C, načet se vyloučený produkt obecného vsorca X odsaje.Alkali metal alkyl 3-aninobeasoate hydrogen sulfates of general X, who R denotes alkyl and 1 to 13 cents of carbon and M denotes sodium or potassium, are suitable for anesthesia of poikilots in vertebrates. Their preparation consists of the tons, is as s and alkyl 3-sninobensoate of formula XX. wherein the above-mentioned result is to treat the sodium or potassium quinquine and sodium quinquine hydrogen sulphate in a polar phosphate nisitslaen with water or, if necessary, with their snow, at a temperature of 20 ° C to 80 ° C.
COORCOOR
Vynález ae týká hydrogenaulfátů alkyl 3-anlhobensoétů alkalických kovů obecného vzoroe Z, kde B anači alkyl a I a* 3 atoay uhlíku a M značí sodík, draslík, která vykazují výrazné anastatické účinky pro polkllotamí obratlovce.The present invention relates to alkali metal alkyl 3-anhobensoetates of the general formula Z, wherein B and C are alkyl and carbon atoms and M are sodium, potassium, which exhibit significant anastatic effects for polyclotamic vertebrates.
Analogická látky ne bésl aetbenoaulfonátů 3-aainobensodtů ae používají jako anestetiku* pro poikiloterani obratlovce. Jejich nevýhoda vtok je, to ve vodná· prostředí uvolňují snačná jedovatou aethanaulfonovou kyselinu.Analogous substances are not 3-aainobensodetes and are used as anesthetics for vertebrate poikiloterani. Their disadvantage is that they release considerable poisonous aethanaulfonic acid in aqueous environments.
Daláí látka, která ao k tonuto účelu poaiívá je propyl 1-/-1-fenylathyl/-5-laldasolkarboyylát, ktorý jo relativná drahý a ápatná biologicky odbouratelný.Another substance which is used for this purpose is propyl 1 - [- 1-phenylathyl] -5-laldasolecarboyylate, which is relatively expensive and biodegradable.
Způaob výroby alkalických hydrogenaulfátů alkyl 3-aalnobensoétů obecného vsorce I, kde 8 a Μ mjí výáe uvedený výsnaa spočívá podle vynálezu v to*, Ie es na alkyl 3-aalnobensoát Obecného vsorce IX, kde R *é shora uvedený výsnan, působí hydrogensulfdto* sodný* nobo draselný* v *olámí* po*áru rsakčních složek 1 : I v prostředí s vodou alsltolnáho polárního organického rospouátádla ao intenaivního *1cháni při taplotá 20 at 80 °C.The process for the preparation of the alkali metal hydrogen sulfates of the alkyl 3-aalnobensoates of general formula (I), wherein the above-mentioned invention is based on the invention, is that the alkyl 3-aalnobensoate of general formula (IX), * noble potassium * in * olamy * after the reaction of 1: 1 component in water with an alsltol polar polar organic surfactant and on intensive drying at a temperature of 20 to 80 ° C.
Jako polární roapouátádlo ao použije alkohol ι 1 al 3 atoay uhlíku nebo aceton, 2-butanon nobo tatrahydrofuran. Postupuje ae tak, la ae k rostoku alkyl 3-aminobenzoátu obecného vaoree II v organická* rospouátádla aa intenaivního míchání přidá po kapkách vodný rontok hydrogenaulfátu sodného něho draselného a po 2 aá 6 hodinách nicháni ae vyloučený produkt obecného vaoree I odfiltruje, pronyje nalýn množství* dřívá snínánáho organického rospouátádla a vysuli.As polar roapouatad o, use will be made of alkohol 1 and 3 atoay carbon alcohol or acetone, 2-butanone nobo-tetrahydrofuran. The procedure is to add dropwise aqueous potassium hydrogen sulphate sulphate and dropwise after 2 to 6 hours and to precipitate the precipitated product of general vauree I, to leave an amount of *. wood of the dreamed organic rospouátadlo and vysuli.
Látky obecného vaoree Z nají a ekologického hlediska celou řadu výhod, nebol obsahuji jako kyselou součást hydrogensulfét alkalického kovu, který jo a hygienického hlediska naprosto bespečný.The general vaoree substances have a number of environmental and environmental advantages, as they do not contain alkali metal hydrogensulfates as an acidic component, which is absolutely brilliant and hygienically acceptable.
PřikladlHe did
K rostoku nothyl 3-eainobensoétu /30 g/ vo 120 al aethanolu bylo přidáno při teplotá místnosti sa intenaivního míchání 24 g hydrogenaulfátu sodného rospuátáného 50 nl vody při toploté 60 aá 70 °C.24 g of sodium hydrogen hydrogen sulphate rospinated with 50 µl of water at 60 ° C to 70 ° C were added to the solution of notyl 3-aminobensoate (30 g) in 120 µL of ethanol at room temperature with intensive stirring.
Po dvou hodinách aichéní byl vyloučený produkt odsát a proayt nalýn *noistvla *ethanolu. Eyio lískáno 43,8 g produktu obecného vsorca I, kde R · CHj, M Na, t.t. 172 ai 175 °C.After two hours of aging, the precipitated product was aspirated and ethanol was removed. Eyio molded 43.8 g of a product of general formula I, wherein R · CH 3, M Na, m.p. 172-175 ° C.
P ř i k 1 a d 2Example 1 and d 2
K rostoku 32,8 g ethyl 3-aninobensodtu ve 120 *1 ethanolu bylo přidáno při taplotá reakční anáal 60 a* 70 °C 24 g hydrogenaulfátu sodného rospuátáného v 55 *1 vody při teplotá 70 °C. Po analogické* spracování reakční aaáal jako v přikladu 1 bylo slakéno 47,5 g produktu obecného vsorca 1, kde R CgHj, N Na, t.t. 133 aá 134 °C.To the solution of 32.8 g of ethyl 3-aninobensodt in 120 * 1 ethanol was added at reaction temperature 60 ° C and 70 ° C 24 g of sodium hydrogen sulphate rospinated in 55% water at 70 ° C. After analogous work-up as in Example 1, 47.5 g of a product of general formula 1 wherein R @ 8 C8 H5 N Na, m.p. Mp 133-134 ° C.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS8410646A CS243441B1 (en) | 1984-12-29 | 1984-12-29 | Hydrogen sulphates of alkaline metals' acryl 3-aminobenzoates and method of their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS8410646A CS243441B1 (en) | 1984-12-29 | 1984-12-29 | Hydrogen sulphates of alkaline metals' acryl 3-aminobenzoates and method of their production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS1064684A1 CS1064684A1 (en) | 1985-08-15 |
| CS243441B1 true CS243441B1 (en) | 1986-06-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS8410646A CS243441B1 (en) | 1984-12-29 | 1984-12-29 | Hydrogen sulphates of alkaline metals' acryl 3-aminobenzoates and method of their production |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS243441B1 (en) |
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1984
- 1984-12-29 CS CS8410646A patent/CS243441B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS1064684A1 (en) | 1985-08-15 |
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