CH91109A - Process for the preparation of silver thioisovalerylamino sodium salicylate. - Google Patents
Process for the preparation of silver thioisovalerylamino sodium salicylate.Info
- Publication number
- CH91109A CH91109A CH91109DA CH91109A CH 91109 A CH91109 A CH 91109A CH 91109D A CH91109D A CH 91109DA CH 91109 A CH91109 A CH 91109A
- Authority
- CH
- Switzerland
- Prior art keywords
- silver
- sodium salicylate
- thioisovalerylamino
- preparation
- sulfide
- Prior art date
Links
- -1 silver thioisovalerylamino sodium salicylate Chemical compound 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 claims description 3
- 229960004025 sodium salicylate Drugs 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- LPSWFOCTMJQJIS-UHFFFAOYSA-N sulfanium;hydroxide Chemical compound [OH-].[SH3+] LPSWFOCTMJQJIS-UHFFFAOYSA-N 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 229910021607 Silver chloride Inorganic materials 0.000 claims 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000003378 silver Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- HFAUMPWMNPYULN-UHFFFAOYSA-N 2-bromo-3-methylbutanoyl bromide Chemical compound CC(C)C(Br)C(Br)=O HFAUMPWMNPYULN-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- XQCGKLLVUIQYJJ-UHFFFAOYSA-N CC(C)CC(NOC(C(C(O)=O)=CC=C1)=C1Br)=O Chemical compound CC(C)CC(NOC(C(C(O)=O)=CC=C1)=C1Br)=O XQCGKLLVUIQYJJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000003372 organotropic effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003441 thioacyl group Chemical group 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
Verfahren zur Darstellung von Silberthioisovalerylaminonatrlumsalicylat. Es ist bekannt, dass die Alkalisalze der Thioglykolsäure mit Silbersalzen Komplex verbindungen eingehen, in welchen das Silber als komplexes Anion vorhanden ist und sich mit den gebräuchlichen Reagenzien rieht mehr nachweisen läisst (Rosenheim, Ztschr.f.anorg. Chemie 41 (1904| S.231). Diese komplex bildende Fähigkeit der Thioacylgruppe ist wie gefunden wurde, auch vorhanden, wenn sie in aromatische Verbindungen eingeführt wird.
Die Bildung solcher komplexer Silberver bindungen, in welchen die komplexbildende Komponente einen substituierten oder nicht substituierten aromatischen Kern enthält, ist von grosser Wichtigkeit, indem die Einfüh rung der verschiedenen aromatischen Kerne gestattet, die chemischen und biochemischen Eigenschaften der Silbersalze in mannigfacher Weise zu verändern und so die parasitotropen und organotropen Fähigkeiten der Silberver bindungen zweckmässig einzustellen.
Gegenstatand x der vorliegenden Erfindung ist ein Verfahren zur Darstellung von Silber- tlrioisovalerylaminonatriumsalicylat, darin be stehend, dass man auf Thioisovalerylamino- natriumsalicvlat Silbersalze einwirken lässt Das Silberthioisovalerylaminonatriumsalicylat reagiert alkalisch. Es ist in Wasser leicht löslieh und scheidet weder auf Zusatz von Schwefelwasserstoffwasser oder Ammonsulfid Silbersulfid ab.
Es soll für therapeutische Zwecke Ver wendung finden.
Beispiel: 2 Tfeile Thioisovalerylaminosalicylsäure (hergestellt durch Umsetzung von Aminosali- cylsäure mit Bromisovalerylbromid in alkali scher Lösung und Ausfällen der entstandenen Bromisovalerylaminosalicylsäure mit Salzsäure; die Bromisovalerylsalicylsäure wird in alka lischer Lösung mit Natriundisulfid versetzt und das Reaktionsprodukt mit Salzsäure ge fällt) werden in 20 Teilen absolutem Alkohol gelöst lund mnit einer Lösung von 0,17 Teilen Natrium in 20 Teilen absolutere Alkohol ver setzt. Das Reaktionsprodukt wird reit Äther gefällt und rasch abgesaugt. 10 Teile des so entstandenen @hioisova@erv@aminonatrium- salievlates werden reit 1.2 Teilen Silbernitrat gut verrieben.
Die so erhaltene, alkalisch reagierende komplexe Verbindung ist in Was ser leicht löslich.
Process for the preparation of silver thioisovalerylamino sodium salicylate. It is known that the alkali salts of thioglycolic acid form complex compounds with silver salts, in which the silver is present as a complex anion and can be more easily detected with the usual reagents (Rosenheim, Ztschr.f.anorg. Chemie 41 (1904 | p. 231) This complex-forming ability of the thioacyl group is found to be also present when it is introduced into aromatic compounds.
The formation of such complex silver compounds, in which the complex-forming component contains a substituted or unsubstituted aromatic nucleus, is of great importance since the introduction of the various aromatic nuclei allows the chemical and biochemical properties of the silver salts to be changed in many ways and so on expediently adjust the parasitotropic and organotropic capabilities of the Silberver compounds.
Object x of the present invention is a process for the preparation of silver tlrioisovalerylamino sodium salicylate, which consists of allowing thioisovalerylamino sodium salicylate to act on silver salts. The silver thioisovalerylamino sodium salicylate has an alkaline reaction. It is easily soluble in water and does not separate on the addition of hydrogen sulfide water or ammonium sulfide silver sulfide.
It should be used for therapeutic purposes.
Example: 2 parts of thioisovalerylaminosalicylic acid (prepared by reacting aminosalicylic acid with bromoisovaleryl bromide in an alkaline solution and precipitating the resulting bromoisovalerylaminosalicylic acid with hydrochloric acid; the bromisovalerylsalicylic acid is mixed with 20 parts of sodium disulphide in an alkaline solution Alcohol dissolved and set with a solution of 0.17 part of sodium in 20 parts of more absolute alcohol. The reaction product is precipitated with ether and quickly sucked off. 10 parts of the @ hioisova @ erv @ aminonatrium-salievlate created in this way are rubbed well with 1.2 parts of silver nitrate.
The alkaline complex compound thus obtained is easily soluble in water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH91109T | 1920-12-01 | ||
| CH90809T | 1920-12-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH91109A true CH91109A (en) | 1922-01-16 |
Family
ID=25704250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH91109D CH91109A (en) | 1920-12-01 | 1920-12-01 | Process for the preparation of silver thioisovalerylamino sodium salicylate. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH91109A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2548257A (en) * | 1948-07-02 | 1951-04-10 | Ward Blenkinsop & Co Ltd | Para-hippurylamido salicylic acids and derivatives and process of manufacture |
-
1920
- 1920-12-01 CH CH91109D patent/CH91109A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2548257A (en) * | 1948-07-02 | 1951-04-10 | Ward Blenkinsop & Co Ltd | Para-hippurylamido salicylic acids and derivatives and process of manufacture |
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