DE551421C - Process for the representation of complex gold compounds - Google Patents
Process for the representation of complex gold compoundsInfo
- Publication number
- DE551421C DE551421C DEF56248D DEF0056248D DE551421C DE 551421 C DE551421 C DE 551421C DE F56248 D DEF56248 D DE F56248D DE F0056248 D DEF0056248 D DE F0056248D DE 551421 C DE551421 C DE 551421C
- Authority
- DE
- Germany
- Prior art keywords
- gold
- solution
- compounds
- water
- thiourea
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002344 gold compounds Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
- 150000001260 acyclic compounds Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 150000002343 gold Chemical class 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 description 1
- FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 1
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- VTYFEQXFCWYKDR-UHFFFAOYSA-N benzoic acid thiourea Chemical compound NC(N)=S.OC(=O)C1=CC=CC=C1 VTYFEQXFCWYKDR-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- CQVNZICBXZRFTM-UHFFFAOYSA-N gold;urea Chemical compound [Au].NC(N)=O CQVNZICBXZRFTM-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- -1 mercapto compound Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/66—Thiobarbituric acids
- C07D239/68—Salts of organic bases; Organic double compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von komplexen Goldverbindungen In dem Patent 537 897 ist ein Verfahren zur Darstellung von komplexen Goldverbindungen beschrieben, dadurch gekennzeichnet, daß man auf Thiobenzimidazole, also auf heterocyclische Verbindungen mit einem kondensierten Kern, Goldsalze einwirken läßt.Process for the preparation of complex gold compounds The patent 537 897 describes a process for the preparation of complex gold compounds, characterized in that gold salts are allowed to act on thiobenzimidazoles, that is to say on heterocyclic compounds with a condensed core.
Bei weiterer Durchforschung dieses Arbeitsgebietes wurde nun die Beobachtung gemacht, daß die Darstellung von Goldverbindungen keineswegs auf die Verwendung dieser vom Thioharnstoff sich ableitenden Verbindungen beschränkt ist, daß vielmehr auch andere sich vom Thioharnstoff ableitende heterocyclische Verbindungen ohne einen kondensierten Kern, z. B. Thiobarbitursäure, ferner acyclische Verbindungen, z. B. Thiohydantoinsäure, zur Darstellung von komplexen Goldverbindungen geeignet sind. Die Einwirkung von Goldsalzen auf Dimethylthioharnstoff ist zwar bereits beschrieben (s. Liebigs Annalen, Bd.285, 1895, S. 17o), das Reaktionsprodukt ist aber keine Metallmercaptoverbindung, sondern ein Golddoppelsalz, es enthält noch das Anion des verwendeten Goldsalzes. Offenbar zeigen die Alkylverbindungen des Thioharnstoffs ein gegenüber Goldsalzen anderes Verhalten als die übrigen Abkömmlinge des Thioharnstoffs, wie sie bei dem vorliegenden Verfahren benutzt werden.With further investigation of this field of work, the observation made that the representation of gold compounds is by no means based on the use these compounds derived from thiourea is limited to that rather also other heterocyclic compounds derived from thiourea without a condensed core, e.g. B. thiobarbituric acid, also acyclic compounds, z. B. thiohydantoic acid, suitable for the preparation of complex gold compounds are. The effect of gold salts on dimethylthiourea has already been described (see Liebigs Annalen, Vol. 285, 1895, p. 17o), but the reaction product is not Metal mercapto compound, but a gold double salt, it still contains the anion of the gold salt used. Apparently show the alkyl compounds of thiourea a different behavior towards gold salts than the other derivatives of thiourea, as used in the present process.
Diese besitzen die für den Thioharnstoff selbst in seiner isomeren Enolform bereits beschriebene (Journal of the Chemical Society Bd. 89, 29o6, S. 1346 f.; Berichte 38, 1905, S. 28i3) Fähigkeit, mit Goldsalzen sich derart umzusetzen, daß das Wasserstoffatom der Sulfhydrylgruppe durch den Goldrest ersetzt wird. Während diese Goldverbindung des Thioharnstoffes jedoch keine besonderen therapeutischen Eigenschaften besitzt, sind die nach dem vorliegenden Verfahren erhältlichen Goldverbindungen von Thioharnstoffderivaten sehr wirksam gegen Infektionserreger und sind insbesondere mit Erfolg z. B. bei Tuberkulose und Lupus erythematosus verwendbar. Beispiel i 6 g Thiohydantoinsättre werden in 225 ccm Wasser und 45 ccm 2 n-Natronlauge gelöst. Das Ganze wird filtriert und mit so viel verdünnter Salzsäure (1o °i,) versetzt, bis eben Lösung erfolgt ist. Darauf gibt man 4,5 g Kaliumauribromid, in 6o ccm Wasser gelöst, hinzu und saugt die ausfallende komplexe Goldverbindung sofort ab;. die nach dem Auswaschen in 5o ccm Wasser suspendiert und mit z n-Natronlauge gelöst wird. Man gießt die Lösung in 121 Alkohol, saugt das ausfallende Na-Salz ab und wäscht mit Alkohol und :Äther. Beispiel e Zu einer Lösung von i Teil Thiobarbitursäure in ioo Teilen Methylalkohol wird eine Lösung von i Teil Kaliumauribromid in 2o Teilen Methylalkohol gegeben. Man filtriert anfangs von etwas ausfallendem Nebenprodukt ab und gibt nachher nochmals die gleiche Menge Kaliumauribromid hinzu. Das ausgefallene Reaktionsprodukt wird abgesaugt, mit Methylalkohol gewaschen, nutschfeucht in wenig Wasser suspendiert und mit 2 n-Natronlauge in Lösung gebracht. Dann wird wie in Beispiel i verfahren.These have the ability already described for the thiourea itself in its isomeric enol form (Journal of the Chemical Society Vol. 89, 29o6, pp. 1346 f .; Reports 38, 1905, pp. 28i3) to react with gold salts in such a way that the Hydrogen atom of the sulfhydryl group is replaced by the gold radical. While this gold compound of thiourea has no special therapeutic properties, the gold compounds of thiourea derivatives obtainable by the present process are very effective against infectious agents and are particularly successful, for. B. can be used in tuberculosis and lupus erythematosus. Example i 6 g of thiohydantoin saturation are dissolved in 225 cc of water and 45 cc of 2N sodium hydroxide solution. The whole thing is filtered and so much dilute hydrochloric acid (10 ° 1) is added until solution has just taken place. 4.5 g of potassium auribromide, dissolved in 60 ccm of water, are then added and the complex gold compound which precipitates is immediately suctioned off. which, after washing, is suspended in 50 cc of water and dissolved with z n sodium hydroxide solution. The solution is poured into alcohol, the precipitated Na salt is suctioned off and washed with alcohol and: ether. Example e A solution of 1 part potassium auribromide in 2o parts methyl alcohol is added to a solution of 1 part thiobarbituric acid in 100 parts methyl alcohol. Initially, some by-product which has precipitated out is filtered off and the same amount of potassium auribromide is then added again. The precipitated reaction product is filtered off with suction, washed with methyl alcohol, dampened with suction, suspended in a little water and brought into solution with 2N sodium hydroxide solution. Then proceed as in example i.
Beispiel 3 159 Monophenylthioharnstoff werden in 20o ccm Essigester gelöst und langsam mit einer Lösung von 34 g Kaliumauribromid in 34 ccm Essigester vereinigt. Unter völliger Entfärbung der Flüssigkeit scheidet sich nach einiger Zeit ein grauer, flockiger Niederschlag eines Nebenproduktes ab, der nach dem Stehen über Nacht abgesaugt wird.Example 3 159 monophenylthiourea are dissolved in 20 ° cc of ethyl acetate dissolved and slowly with a solution of 34 g of potassium auribromide in 34 cc of ethyl acetate united. With complete discoloration of the liquid, it separates after a while Time a gray, fluffy precipitate of a by-product that appears after standing is suctioned off overnight.
Das Filtrat hinterläßt nach dem Abdestillieren im Vakuum einen Rückstand, der beim Verreiben mit Wasser zu einem gelbgrünem Pulver erstarrt. Dieses Produkt wird abgesaugt, mit Wasser gewaschen und im Hochvakuum getrocknet. Das neue Goldpräparat ist in den üblichen Lösungsmitteln unlöslich. Beispiel 4 35g Diphenylthioharnstoff werden in 1,51 Essigester gelöst und tropfenweise mit einer Lösung von io g Kaliumauribromid in ioo ccm Essigester versetzt. Es scheidet sich sofort ein körniger, gelber Niederschlag aus, der nach kurzem Nachrühren abgesaugt, mit wenig Essigester nachgewaschen und im Hochvakuum getrocknet wird. Dieses Goldpräparat ist ebenfalls in den üblichen Lösungsmitteln unlöslich. Beispiel s 5 g Thioharnstoffbenzoesäure (s. Beilstein, 3. Aufl., Bd. II, S. 1264) werden in 30o ccm Sprit suspendiert und allmählich mit einer Lösung von 6 g Kaliumauribromid in 6 ccm Sprit vereinigt. Unter Entfärbung der Flüssigkeit geht die suspendierte Harnstoffcarbonsäure in Lösung. Dafür beginnt sich nach kurzer Zeit ein grauer Niederschlag eines Nebenproduktes abzuscheiden, der nach dem Stehen über Nacht abgesaugt wird. Aus dem Filtrat scheidet sich beim Verdünnen mit z 1 Wasser die Goldharnstoffcarbonsäure als gelber Niederschlag aus, der abgesaugt, mit Wasser gewaschen und im Hochvakuum getrocknet wird.After distilling off in vacuo, the filtrate leaves a residue, which solidifies to a yellow-green powder when rubbed with water. This product is filtered off with suction, washed with water and dried in a high vacuum. The new gold preparation is insoluble in common solvents. Example 4 35g diphenylthiourea are dissolved in 1.5 l of ethyl acetate and added dropwise with a solution of 10 g of potassium auribromide added to 100 cc of ethyl acetate. A granular, yellow precipitate separates out immediately off, which after brief stirring is suctioned off, washed with a little ethyl acetate and is dried in a high vacuum. This gold preparation is also in the usual Solvent insoluble. Example s 5 g of thiourea benzoic acid (see Beilstein, 3rd edition, Vol. II, p. 1264) are suspended in 30o ccm of fuel and gradually with combined a solution of 6 g of potassium auribromide in 6 ccm of fuel. Under discoloration the suspended urea carboxylic acid goes into solution in the liquid. For that begins after a short time a gray precipitate of a by-product is deposited, which is suctioned off after standing overnight. From the filtrate separates from the Dilute the gold urea carboxylic acid with z 1 water as a yellow precipitate, which is filtered off with suction, washed with water and dried in a high vacuum.
Die Säure läßt sich durch Behandlung mit der berechneten Menge verdünnter Natronlauge in die wasserlöslichen Alkalisalze überführen. Beispiel 6 43,2 Teile m-W-Allylthioharnstoffbenzoesäure werden in 96o Teilen absolutem Alkohol gelöst und mit einer Lösung von 54 Teilen Kaliumauribromid in 43o Teilen absolutem 'Alkohol versetzt. Nach dem Stehen über Nacht wird die hellgelbe Lösung von ausgeschiedenem Bromkalium filtriert und mit Natriumäthylatlösung neutralisiert. Die Fällung des Natriumsalzes der Auroallylthioharnstoffbenzoesäure wird durch Zugabe von Äther vervollständigt, worauf abgesaugt, mit Äther gewaschen und im Vakuumexsikkator getrocknet wird.The acid can be diluted by treating it with the calculated amount Convert caustic soda into the water-soluble alkali salts. Example 6 43.2 parts m-W-Allylthioureabenzoic acid is dissolved in 96o parts of absolute alcohol and with a solution of 54 parts of potassium auribromide in 43o parts of absolute alcohol offset. After standing overnight, the light yellow solution of excreted Filtered potassium bromide and neutralized with sodium ethylate solution. The precipitation of the The sodium salt of auroallylthioureabenzoic acid is made by adding ether completed, whereupon suctioned off, washed with ether and dried in a vacuum desiccator will.
Zur Reindarstellung der Goldverbindung wird das so gewonnene Rohprodukt mit Wasser gelöst und mit verdünnter Säure angesäuert. Die hierdurch gefällte Goldsäure wird in einer Zentrifuge abgeschleudert, mit Wasser gewaschen und mit der berechneten Menge Natriumbicarbonat in Wasser gelöst. Durch Einfließenlassen der filtrierten Lösung in ein Alkoholäthergemisch fällt das auroallylthioharnstoffbenzoesaure Natrium aus, welches abgesaugt, mit Äther gewaschen und im Vakuumexsikkator getrocknet wird. Die Substanz stellt ein feines gelbes bis gelbbraunes Pulver dar und ist leicht löslich in Wasser.The crude product obtained in this way is used to make the gold compound pure dissolved with water and acidified with dilute acid. The thereby precipitated gold acid is spun in a centrifuge, washed with water and calculated with the Amount of sodium bicarbonate dissolved in water. By flowing in the filtered Solution in an alcohol ether mixture falls the auroallylthioureabenzoic acid sodium from, which is suctioned off, washed with ether and dried in a vacuum desiccator. The substance is a fine yellow to yellow-brown powder and is light soluble in water.
Claims (1)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL15796D NL15796C (en) | 1923-12-07 | ||
| DEF56248D DE551421C (en) | 1923-12-07 | 1924-06-02 | Process for the representation of complex gold compounds |
| AT102313D AT102313B (en) | 1923-12-07 | 1924-11-28 | Process for the representation of complex gold compounds. |
| CH119640D CH119640A (en) | 1924-06-02 | 1924-12-04 | Process for the preparation of a complex gold compound of thiohydantoic acid. |
| CH117443D CH117443A (en) | 1924-06-02 | 1924-12-04 | Process for the preparation of a complex gold compound of thiohydantoic acid. |
| GB2945924A GB234772A (en) | 1923-12-07 | 1924-12-08 | Manufacture of complex gold compounds |
| CH125640D CH125640A (en) | 1924-06-02 | 1927-02-04 | Process for the preparation of a gold compound of w-allylthioureabenzoic acid. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF55092D DE537897C (en) | 1923-12-07 | 1923-12-07 | Process for the preparation of gold compounds of the thiobenzimidazole series |
| DEF56248D DE551421C (en) | 1923-12-07 | 1924-06-02 | Process for the representation of complex gold compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE551421C true DE551421C (en) | 1932-06-02 |
Family
ID=25977672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF56248D Expired DE551421C (en) | 1923-12-07 | 1924-06-02 | Process for the representation of complex gold compounds |
Country Status (4)
| Country | Link |
|---|---|
| AT (1) | AT102313B (en) |
| DE (1) | DE551421C (en) |
| GB (1) | GB234772A (en) |
| NL (1) | NL15796C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2827462A (en) * | 1953-01-02 | 1958-03-18 | Union Oil Co | Werner complexes |
| US5049484A (en) * | 1990-11-16 | 1991-09-17 | Eastman Kodak Company | Photographic silver halide material and process |
-
0
- NL NL15796D patent/NL15796C/xx active
-
1924
- 1924-06-02 DE DEF56248D patent/DE551421C/en not_active Expired
- 1924-11-28 AT AT102313D patent/AT102313B/en active
- 1924-12-08 GB GB2945924A patent/GB234772A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB234772A (en) | 1926-03-08 |
| AT102313B (en) | 1926-01-11 |
| NL15796C (en) |
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