CH193835A - Method for producing a urethane series mercury compound. - Google Patents
Method for producing a urethane series mercury compound.Info
- Publication number
- CH193835A CH193835A CH193835DA CH193835A CH 193835 A CH193835 A CH 193835A CH 193835D A CH193835D A CH 193835DA CH 193835 A CH193835 A CH 193835A
- Authority
- CH
- Switzerland
- Prior art keywords
- mercury
- salt
- mercury salt
- urethane
- compound
- Prior art date
Links
- -1 urethane series mercury compound Chemical class 0.000 title claims description 6
- 229940100892 mercury compound Drugs 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000002730 mercury Chemical class 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- 150000001875 compounds Chemical group 0.000 claims description 5
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 229910000474 mercury oxide Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- OFIHJYLASXZYAR-UHFFFAOYSA-N [Hg](=O)=O Chemical compound [Hg](=O)=O OFIHJYLASXZYAR-UHFFFAOYSA-N 0.000 claims description 2
- 230000002421 anti-septic effect Effects 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000002934 diuretic Substances 0.000 claims description 2
- 230000001882 diuretic effect Effects 0.000 claims description 2
- 150000002731 mercury compounds Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 150000003673 urethanes Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
- C07F3/103—Mercury compounds without C-Mercury linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer Quecksilberverbindung der Urethanreihe. Es wurde gefunden, dass man zu einer neuen Quecksilberverbindung gelangen kann, wenn man auf N-Allyl-isopropylurethan ein Merkurisalz einwirken lässt und aus dem so erhaltenen Salz die Base in Freiheit setzt.
Die auf diese Weise gewonnene Verbin dung der Konstitutionsformel
EMI0001.0006
bildet ein weisses Kristallpulver, das gegen Natronlauge beständig ist. Die neue Verbin dung bildet wasserlösliche Salze. Ihr Acetat hat den F. 91-92 .
Die neue Verbindung zeichnet sich durch ihre starke diuretische und antiseptische Wir kung bei guter Verträglichkeit aus. Sie soll therapeutische Verwendung finden.
Nach dem Verfahren der Erfindung wird die gleiche Verbindung erhalten; sowohl durch die Addition normaler, als auch basischer Merkurisalze, wie zum Beispiel den aus einer Mischung von je 1 DZol Merkurioxyd und 1 Äquivalent einer organischen Säure, oder je 1/2 112o1 Merkurioxyd und 1/2 Mol eines normalen Merkurisalzes ' erhaltenen Salzen.
<I>Beispiel:</I> 14,3 Teile N-Allyl-isopropylurethan (Kp4 73-74 , dargestellt aus Allylamin und Chlor- ameisensäureisopropylester), 15,9 Teile Mer- kuriacetat und 10,8 Teile Merkurioxyd werden mit Wasser bis zur vollständigen Umsetzung erwärmt und die filtrierte Lösung einge dampft. Das so erhaltene Öl erstarrt bald und kann aus Essigester umkristallisiert werden.
Zur Herstellung der freien. Base wird das so gewonnene N-Allyl-isopropylurethan-mer- kuriacetat mit der berechneten Menge Natron lauge versetzt und die Lösung im Vakuum eingedampft. Durch Ausziehen mit absolutem Alkohol und Verdampfen des Lösungsmittels erhält inan das N-Allyl-isopropylurethan-mer- kurihydroxyd. An Stelle von Merkuriacetat kann auch ein anderes Merkurisalz, oder auch Merkurioxyd in Gegenwart von 1 Äquivalent einer organischen Säure verwendet werden.
A method for producing a urethane series mercury compound. It has been found that a new mercury compound can be obtained if a mercury salt is allowed to act on N-allyl-isopropyl urethane and the base is released from the salt thus obtained.
The connection of the constitutional formula obtained in this way
EMI0001.0006
forms a white crystal powder that is resistant to caustic soda. The new compound forms water-soluble salts. Your acetate has the F. 91-92.
The new compound is characterized by its strong diuretic and antiseptic effects and is well tolerated. It should find therapeutic use.
According to the process of the invention the same compound is obtained; both by the addition of normal as well as basic mercury salts, such as the salts obtained from a mixture of 1 DZol each of mercury dioxide and 1 equivalent of an organic acid, or 1/2 112o1 of mercury oxide and 1/2 mol of a normal mercury salt.
<I> Example: </I> 14.3 parts of N-allyl-isopropyl urethane (Kp4 73-74, prepared from allylamine and isopropyl chloroformate), 15.9 parts of mercuric acetate and 10.8 parts of mercuric oxide are mixed with water to heated to complete implementation and the filtered solution evaporated. The oil obtained in this way soon solidifies and can be recrystallized from ethyl acetate.
To make the free. Base, the N-allyl-isopropyl urethane mercuriacetate obtained in this way is mixed with the calculated amount of sodium hydroxide solution and the solution is evaporated in vacuo. By extraction with absolute alcohol and evaporation of the solvent, the N-allyl-isopropyl urethane mercury hydroxide is obtained. Instead of mercury acetate, another mercury salt, or even mercury oxide, can be used in the presence of 1 equivalent of an organic acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH193835T | 1934-11-03 | ||
| CH188440T | 1935-09-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH193835A true CH193835A (en) | 1937-10-31 |
Family
ID=25721640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH193835D CH193835A (en) | 1934-11-03 | 1934-11-03 | Method for producing a urethane series mercury compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH193835A (en) |
-
1934
- 1934-11-03 CH CH193835D patent/CH193835A/en unknown
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