CH288024A - Process for the preparation of pyridyl-3-aldehyde thiosemicarbazone. - Google Patents
Process for the preparation of pyridyl-3-aldehyde thiosemicarbazone.Info
- Publication number
- CH288024A CH288024A CH288024DA CH288024A CH 288024 A CH288024 A CH 288024A CH 288024D A CH288024D A CH 288024DA CH 288024 A CH288024 A CH 288024A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyridyl
- aldehyde
- preparation
- water
- aldehyde thiosemicarbazone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000005187 foaming Methods 0.000 description 1
- -1 for example Chemical class 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000000766 tuberculocidal effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung von Pyridyl-3-aldehyd-thiosemiearbazon. Es wurde gefunden, da.ss das bisher unbe kannte Thiosemicarbazon des Pyridyl-3-alde- hyds in v ivo ausgezeichnete tuberkulocide Wirkungen zeigt.
Das Pyridyl-3-aldehyd-thio- semiearbazon zeichnet sich durch eine gute Verträglichkeit aus und weist vor bekannten Verbindungen dieser Reihe bestimmte Vorzüge auf;
so lassen sich infolge des amphoteren Charakters der Verbindung sowohl wasser lösliche Salze mit anorganischen und organi schen Säuren als auch wasserlösliche Salze mit anorganischen und organischen Basen, wie zum Beispiel Li, Na, Ka., Mg und Tetra- alkylamnioniumliydroa-yd, herstellen.
Das Pyr idyl. - 3 - aldehyd-thiosemiearbazon lässt sieh aus dein Pyridyl-3-aldehyd (vgl. Panimon, Helvetica Chimica Acta [1941], Bd. 24, S. 24F-28 E) und Thiosemicarbazid nach den üblichen Methoden in ausgezeich neter Ausbeute darstellen.
Beispiel: Zu einer kochenden Lösung von 10 Cre- wiehtsteilen Py ridyl-3-aldehyd und 10 G e wichtsteilen Alkohol fügt man unter Rühren eine Lösung von 9,3 Gewichtsteilen Thiosemi- earbazid in 30 Raumteilen heissem Wasser. Man erhitzt noch<B>15</B> Minuten zum Sieden, kühlt, saugt den Niederschlag ab und wäscht ihn mit kaltem Alkohol und Äther aus.
Man erhält das Pyridyl-3-aldehyd-thiosemicarbazon in Form farbloser, derber Kristalle, die, aus Wasser umkristallisiert, bei 206 bis 207 C un ter Aufschäumen schmelzen. Die Ausbeute bei dieser Umsetzung beträgt. mehr als 80 % der Theorie. Die Verbindung ist in kaltem Wasser wenig, in heissem beträchtlich löslich und bildet sowohl mit anorganischen und or ganischen Säuren als auch mit starken Basen wasserlösliche Salze.
Process for the preparation of pyridyl-3-aldehyde thiosemiearbazon. It has been found that the previously unknown thiosemicarbazone of pyridyl-3-aldehyde shows excellent tuberculocidal effects in vivo.
The pyridyl-3-aldehyde-thio- semiearbazon is characterized by a good compatibility and has certain advantages over known compounds of this series;
Thus, due to the amphoteric character of the compound, both water-soluble salts with inorganic and organic acids and water-soluble salts with inorganic and organic bases, such as, for example, Li, Na, Ka., Mg and tetraalkylamnionium hydroxide, can be prepared.
The pyr idyl. - 3 - Aldehyde-thiosemicarbazon can be prepared from your pyridyl-3-aldehyde (cf. Panimon, Helvetica Chimica Acta [1941], Vol. 24, pp. 24F-28 E) and thiosemicarbazide by the usual methods in excellent yield.
Example: A solution of 9.3 parts by weight of thiosemi-earbazide in 30 parts by volume of hot water is added to a boiling solution of 10 parts by weight of pyridyl-3-aldehyde and 10 parts by weight of alcohol. The mixture is heated to boiling for <B> 15 </B> minutes, cooled, the precipitate is filtered off with suction and washed out with cold alcohol and ether.
The pyridyl-3-aldehyde thiosemicarbazone is obtained in the form of colorless, coarse crystals which, recrystallized from water, melt at 206 to 207 ° C. under foaming. The yield in this reaction is. more than 80% of theory. The compound is not very soluble in cold water and considerably soluble in hot water, and forms water-soluble salts with inorganic and organic acids as well as with strong bases.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH288024T | 1950-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH288024A true CH288024A (en) | 1952-12-31 |
Family
ID=4486049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH288024D CH288024A (en) | 1950-06-09 | 1950-06-09 | Process for the preparation of pyridyl-3-aldehyde thiosemicarbazone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH288024A (en) |
-
1950
- 1950-06-09 CH CH288024D patent/CH288024A/en unknown
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