DE538375C - Process for the preparation of organic mercury compounds - Google Patents
Process for the preparation of organic mercury compoundsInfo
- Publication number
- DE538375C DE538375C DEI37480D DEI0037480D DE538375C DE 538375 C DE538375 C DE 538375C DE I37480 D DEI37480 D DE I37480D DE I0037480 D DEI0037480 D DE I0037480D DE 538375 C DE538375 C DE 538375C
- Authority
- DE
- Germany
- Prior art keywords
- mercury
- preparation
- water
- mercury compounds
- organic mercury
- 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
- 150000002731 mercury compounds Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000002730 mercury Chemical class 0.000 claims description 2
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 claims description 2
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- BTFHIKZOEZREBX-UHFFFAOYSA-N 3,7-dimethyl-1-prop-2-enylpurine-2,6-dione Chemical compound CN1C(=O)N(CC=C)C(=O)C2=C1N=CN2C BTFHIKZOEZREBX-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229940100892 mercury compound Drugs 0.000 description 3
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- -1 Mercury acetate Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- ZGIBYCLLIMGXEZ-UHFFFAOYSA-N 1,3-dimethyl-7-prop-2-enylpurine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CC=C)C=N2 ZGIBYCLLIMGXEZ-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- HIVLDXAAFGCOFU-UHFFFAOYSA-N ammonium hydrosulfide Chemical compound [NH4+].[SH-] HIVLDXAAFGCOFU-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001550 time effect Effects 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
- C07F3/14—Heterocyclic substances containing mercury
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von organischen Quecksilberverbindungen Es wurde gefunden, daß man durch Einwirkung von Quecksilbersalzen, wie beispielsweise Quecksilberacetat, auf Purinderivate, welche eine ungesättigte Seitenkette enthalten, wie beispielsweise Allyltheobromin, Allyltheophyllin u. a., zu Verbindungen gelangt, in welchen das Quecksilber an der Seitenkette durch Aufhebung der Doppelbindung fixiert ist.Process for the preparation of organic mercury compounds It has been found that by the action of mercury salts, such as Mercury acetate, on purine derivatives that contain an unsaturated side chain, such as allyl theobromine, allyl theophylline and others, leads to compounds, in which the mercury on the side chain by breaking the double bond is fixed.
Die Verbindungen haben sich als wertvolle Arzneimittel, speziell als starke Diuretika, erwiesen und sollen daher in der Therapie Verwendung finden. Beispiel 1 22g 1-Allyltheobrornin (vgl. Chemisches Zentralblatt 1921, IV, 1049) werden: in 5ooccm Methanol gelöst und unter Schütteln mit 31,86g Mercuriacetat in 5oo ccm Wasser versetzt. Die alsbald klar werdende Flüssigkeit wird bei Zimmertemperatur 24 Stunden geschüttelt. Das Ganze wird dann im Vakuum eingedampft und der Rückstand mit Chloroform ausgezogen. Nach dem Trocknen des Chloroforms wird auf die Hälfte eingeengt und diese konzentrierte Chloroformlösung auf Petroläther getropft, wobei die Quecksilberverbindung in reiner Form als weißes Pulver ausfällt. Die neue Quecksilberverbindung ist in Wasser verhältnismäßig leicht löslich.The compounds have proven to be valuable medicines, specifically as strong diuretics, proven and should therefore be used in therapy. example 1 22g of 1-allyl theobromine (cf. Chemisches Zentralblatt 1921, IV, 1049) are: in Dissolved 5ooccm of methanol and shaking with 31.86g of mercuric acetate in 5oo ccm of water offset. The liquid, which soon becomes clear, is at room temperature for 24 hours shaken. The whole is then evaporated in vacuo and the residue with chloroform moved out. After the chloroform has dried, it is concentrated to half and this concentrated chloroform solution was added dropwise to petroleum ether, the mercury compound precipitates in pure form as a white powder. The new mercury compound is in Relatively easily soluble in water.
Beispiel 2 229 7-Allyltheophyllin (vgl. F r i e d l ä n -d e r, Fortschritte der Teerfarbenfabrikation, Bd. 14.,[r9261 S. 1325) -,verden in:45occmMethylalkoliol gelöst und 22 Stunden mit einer Lösung von 31,86g Mercuriacetat in. 5ooccm Wasser geschüttelt. Das Ganze wird danach im Vakuum eingedampft und der Rückstand in Wasser gelöst. Nachdem die wässerige Lösung mit Natriumcarbonat neutralisiert ist, wird sie mit Chloroform ausgezogen. Aus der Chloroformlösung wird ein goldgelbes Öl erhalten, das die Anlag erungsverbindung des Quecksilberacetats an Allyltheophyll,in darstellt. Dieselbe kann durch Schütteln: in Wasser mit einer gesättigten Natriumchloridlösung in die entsprechende Chlorverbindung übergeführt werden, welcher auf Grund der Analysenzahlen die Formel C10 His 0s N4 - Hg Cl # H2 O zukommt (ber. 40,9 % 119, gef. 41,3 0% H"). Der Schmelzpunkt der Chlorverbindung ist 184 bis 186°. Beispiel 3 22g Allyltheobromin in; 5oo ccm Methylalkohol gelöst, werden mit den Lösungen aus 27,2g Quecksilberchlorid in 5oo ccm Wasser und 8,2g entwässertem Natriumacetat in roo ccm Wasser 12 Stunden geschüttelt. Allmählich scheidet sich die QuecksilberchloridanLagerungsverbindung ab, die abgesaugt und aus Methylalkohol umkristallisiert wird. Sie stellt eine weiße Kristallmasse vom Schmelzpunkt 168 bis 17o° dar, ist in Natronlauge löslich und kann daraus mit Säuren unverändert gefällt werden. Sie enthält q.o,q. % Quecksilber (ber. 40,9 % Hg).Example 2 229 7-Allyl theophylline (cf. F riedlä n -der, advances in tar paint production, Vol. 14., [R9261 p. 1325) -, verden in: 45occm methyl alcohol and treated with a solution of 31.86g mercuric acetate in 50 ooccm of water shaken. The whole is then evaporated in vacuo and the residue is dissolved in water. After the aqueous solution is neutralized with sodium carbonate, it is extracted with chloroform. A golden yellow oil is obtained from the chloroform solution, which is the plant compound of mercury acetate in allyl theophyll. It can be converted into the corresponding chlorine compound by shaking: in water with a saturated sodium chloride solution, which based on the analytical figures has the formula C10 His 0s N4 - Hg Cl # H2 O (calc. 40.9% 119, found 41.3 0% H "). The melting point of the chlorine compound is 184 ° to 186 °. Example 3 22 g of allyl theobromine dissolved in 5oo cc of methyl alcohol are combined with the solutions of 27.2 g of mercury chloride in 500 cc of water and 8.2 g of dehydrated sodium acetate in roo cc of water Shaken for 12 hours. Gradually, the mercury chloride compound separates out, which is sucked off and recrystallized from methyl alcohol. It is a white crystalline mass with a melting point of 168 to 170 °, is soluble in sodium hydroxide solution and can be precipitated from it unchanged with acids. It contains qo, q .% Mercury (calc. 40.9% Hg).
Beispiel ¢ 4,68g r-Allylomethyltheobromin (aus Theobrominnatrium und ARylomethylbromid) in 5o ccm Methylalkohol werden 18 Stunden mit 6,379 Quecksilberacetat in 5o ccm Wasser geschüttelt. Das Ganze wird im Vakuum eingedampft, der Rückstand mit Wasser aufgenommen und neutralisiert. Die neutrale Lösung wird mit Chloroform ausgezogen. Aus dem Chloroform wird lein öl erhalten, das die Quecksilberacetatanlagerungsverbindung an Allylomethyltheobromin darstellt. Durch Versetzen seiner Lösung in Wasser mit Natriumchloridlösung entsteht die entsprechende Chlorverbindung, die durch Umkristallisieren aus Diäthylinwasser rein erhalten wird. Beispiel 7-Allylomethyltheophylhn gibt nach der in Beispiel q. angegebenen Vorschrift die Qnecksilberanlagerungsverbi;ndung von 7 -Allylomethyltheophyllin. Gef. 39,9 %, ber. 39,9 % Hg für C,2 H,7 03 N4. Hg Cl.Example 4,68g ¢ r-Allylomethyltheobromin (from Theobrominnatrium and ARylomethylbromid) in 5o cc of methyl alcohol is shaken for 1 8 hours 6,379 mercuric acetate in 5o cc of water. The whole is evaporated in vacuo, the residue is taken up in water and neutralized. The neutral solution is extracted with chloroform. From the chloroform, linseed oil is obtained, which is the addition of mercury acetate to allylomethyl theobromine. By adding sodium chloride solution to its solution in water, the corresponding chlorine compound is formed, which is obtained in pure form by recrystallization from diethyline water. Example 7-Allylomethyltheophylhn gives according to the example q. given specification, the silver addition compound of 7-allylomethyltheophylline. Found 39.9%, calc. 39.9% Hg for C, 2 H, 7 03 N4. Hg Cl.
In den nach obigen Beispielen erhaltenen Verbindungen ist das Quecksilber komplex gebunden. Es wird miE Natronlauge nicht abgespalten, sondern erst nach längerer Einwirkung von Schwefelammonium in der Wärme.In the compounds obtained according to the above examples, this is mercury complex bound. With caustic soda, it is not split off, but only after a longer period of time Effect of sulfur ammonium in the heat.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI37480D DE538375C (en) | 1929-03-22 | 1929-03-22 | Process for the preparation of organic mercury compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI37480D DE538375C (en) | 1929-03-22 | 1929-03-22 | Process for the preparation of organic mercury compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE538375C true DE538375C (en) | 1934-05-07 |
Family
ID=7189528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI37480D Expired DE538375C (en) | 1929-03-22 | 1929-03-22 | Process for the preparation of organic mercury compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE538375C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1005517B (en) * | 1955-12-30 | 1957-04-04 | Cassella Farbwerke Mainkur Ag | Process for the production of new xanthine compounds containing mercury |
-
1929
- 1929-03-22 DE DEI37480D patent/DE538375C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1005517B (en) * | 1955-12-30 | 1957-04-04 | Cassella Farbwerke Mainkur Ag | Process for the production of new xanthine compounds containing mercury |
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