CH288588A - Verfahren zur Herstellung eines Thiosemicarbazons eines heterocyclischen Aldehyds. - Google Patents
Verfahren zur Herstellung eines Thiosemicarbazons eines heterocyclischen Aldehyds.Info
- Publication number
- CH288588A CH288588A CH288588DA CH288588A CH 288588 A CH288588 A CH 288588A CH 288588D A CH288588D A CH 288588DA CH 288588 A CH288588 A CH 288588A
- Authority
- CH
- Switzerland
- Prior art keywords
- aldehyde
- thiosemicarbazone
- pyridine
- preparation
- heterocyclic
- Prior art date
Links
- -1 heterocyclic aldehyde Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title 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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- QTSJJDIDTYFLFC-UHFFFAOYSA-N (pyridin-4-ylmethylideneamino)thiourea Chemical compound NC(=S)NN=CC1=CC=NC=C1 QTSJJDIDTYFLFC-UHFFFAOYSA-N 0.000 claims description 3
- 150000007857 hydrazones Chemical class 0.000 claims description 3
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 description 3
- 150000003584 thiosemicarbazones Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XSGNECLIVOTMQJ-UHFFFAOYSA-N 1,5-dimethylpyrazole-3-carbaldehyde Chemical compound CC1=CC(C=O)=NN1C XSGNECLIVOTMQJ-UHFFFAOYSA-N 0.000 description 1
- OUKQTRFCDKSEPL-UHFFFAOYSA-N 1-Methyl-2-pyrrolecarboxaldehyde Chemical compound CN1C=CC=C1C=O OUKQTRFCDKSEPL-UHFFFAOYSA-N 0.000 description 1
- NLEHTGOUPMZIMK-UHFFFAOYSA-N 2,4-dimethyl-1h-pyrrole-3-carbaldehyde Chemical compound CC1=CNC(C)=C1C=O NLEHTGOUPMZIMK-UHFFFAOYSA-N 0.000 description 1
- JWYFGNVBKRJGTN-UHFFFAOYSA-N 2,5-dimethylpyrazole-3-carbaldehyde Chemical compound CC=1C=C(C=O)N(C)N=1 JWYFGNVBKRJGTN-UHFFFAOYSA-N 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- OQORFMABOZEDBL-UHFFFAOYSA-N 2-phenylpyrazole-3-carbaldehyde Chemical compound O=CC1=CC=NN1C1=CC=CC=C1 OQORFMABOZEDBL-UHFFFAOYSA-N 0.000 description 1
- VZJJIEBMUWCKJY-UHFFFAOYSA-N 2-phenyltriazole-4-carbaldehyde Chemical compound N1=C(C=O)C=NN1C1=CC=CC=C1 VZJJIEBMUWCKJY-UHFFFAOYSA-N 0.000 description 1
- WCSKIGHLQNUCNV-UHFFFAOYSA-N 4,6-dimethylpyrimidine-2-carbaldehyde Chemical compound CC1=CC(C)=NC(C=O)=N1 WCSKIGHLQNUCNV-UHFFFAOYSA-N 0.000 description 1
- XVYUFMIOZLCWCT-UHFFFAOYSA-N 5-methyl-1-phenylpyrazole-3-carbaldehyde Chemical compound CC1=CC(C=O)=NN1C1=CC=CC=C1 XVYUFMIOZLCWCT-UHFFFAOYSA-N 0.000 description 1
- PCVZRHVWMPIZJP-UHFFFAOYSA-N 5-methyl-2-phenylpyrazole-3-carbaldehyde Chemical compound N1=C(C)C=C(C=O)N1C1=CC=CC=C1 PCVZRHVWMPIZJP-UHFFFAOYSA-N 0.000 description 1
- BMNPVMQSUPTGFD-UHFFFAOYSA-N 6-aminopyridine-3-carbaldehyde Chemical compound NC1=CC=C(C=O)C=N1 BMNPVMQSUPTGFD-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WESRLFHYORXROO-UHFFFAOYSA-N BrC1=C(NC(=C1Br)Br)C=O Chemical compound BrC1=C(NC(=C1Br)Br)C=O WESRLFHYORXROO-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010044756 Tuberculous infections Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BLEQFIQOCMNEBW-UHFFFAOYSA-N pyridin-4-ylmethylidenehydrazine Chemical compound NN=CC1=CC=NC=C1 BLEQFIQOCMNEBW-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000000814 tuberculostatic agent Substances 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
-
- 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
- C07D213/60—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 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 to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Verfahren zur Herstellung eines Thiosemicarbazons eines heterocyclischen Aldehyds. Thiosemicarbazone, die sich von einkerni gen, unsubstituierten oder substituierten hete- rocyclischen Aldehyden mit mindestens einem Stickstoffatom als Ringglied einerseits, und Thiosemicarbazid anderseits ableiten, sind bisher nicht bekannt geworden. Wie gefunden wurde, können sie auf die Entwicklung von Tuberkelinfektionen beim Warmblüter hem mend wirken.
Zugleich ist ihre Toxizität rela tiv niedrig, so dass sie als solche oder in Form ihrer Salze zur Chemotherapie tuber kulöser Infektionen verwendet werden kön nen.
Die neuen Thiosemicarbazone lieterocycli- scher Aldehyde können in für die Herstellung anderer Thiosemicarbazone üblicher Weise hergestellt werden, indem man die oben de finierten Aldehyde oder deren reaktionsfähige funktionelle Derivate zunächst mit Hydrazin in die entsprechenden Hydrazone überführt und auf diese hierauf Rhodanwasserstoffsäure einwirken lässt.
Als heterocyclische Aldehyde seinen bei spielsweise genannt Py rrol-2-aldehyd, N-Methyl-pyrrol-2-aldehyd, 2,4-Dimethyl-pyrrol-3-aldehyd, 3,4, 5-Tribrom-pyrrol-2-aldehyd, 1-Phenyl-pyrazol-5-aldehyd, 1-Phenyl-5-methyl-pyrazol-3-aldeliyd, 1-Phenyl-3-methyl-pyrazol-5-aldehyd, 1,5-Dimethyl-pyrazol-3-aldehyd, 1,3-Dimethyl-pyrazol-5-aldehyd, 1.-Phenyl-3-metliyl-5-pyrazolon-4-aldehyd, 1.-Phenyl-2,
3-dimethyl-5-pyrazolon-4-aldehyd, 3-!VIethyl-isoxazol-5-aldehyd, 5-Methy 1-isoxazol-3-aldehyd, -1-Methyl-thiazol-5-aldehyd, 1-Phenyl-1,2,5-triazol-3-aldehyd, 1-Phenyl-5-methyl-1.,2,3-triazol-4-aldehyd, Pyridin-2-aldehyd, Pyridin-3-aldehyd, Pyridin'-4-aldehyd, ss-Pyridyl- (2) -propionaldehyd, 6-Amino-py ridin-3-aldehyd, 4,6-Dimethyl-pyrimidin-2-aldehyd,
6-Oxy-2,4-diäthyl-pyrimidin-5-aldehyd, LTracil-4-aldehyd, Thymin-4-aldehyd, Cytosin-4-aldehy d, 9=Mercapto-4-oxy-pyriinidin-6-aldehyd.
Gegenstand vorliegenden Patentes ist niui ein Verfahren zur Herstellung eines Thio- semicarbazons eines heterocyclischen Alde hyds. Das Verfahren ist dadurch gekenn zeichnet, dass man eine den Rest
EMI0001.0058
abgebende Verbindung, wie z.
B. Pyridin-4- aldehyd oder seine reaktionsfähigen funk tionellen Derivate, wie das Imin, Oxim oder die Bisulfitadditionsverbindung, mit Hydra zin umsetzt und das erhaltene Hydrazon mit Rhodanwasserstoffsäure behandelt.
Die erhaltene neue Verbindung, das Pyr i- din-4-aldehyd-thiosemicarbazon, zeigt einen Schmelzpunkt von 232 bis 234 . Sie soll als Tuberkulostatikum Verwendung finden.
<I>Beispiel:</I> 2 Teile. Pyridin-4-aldehyd-hydrazon (Kpl3 154 bis 155 , hergestellt durch Zugabe von Pyridin-4-aldeh)7d zu einem überschuss von Hydrazinhydrat in Alkohol unter Kühlung und anschliessende Destillation) und 1,3 Teile trockenes Ammonium-rhodanid in 10 Teilen abs. Alkohl werden mit so viel konz. Salz säure versetzt, dass die Lösung gerade lack- inttssauer reagiert.
Sie wird 3 Stunden auf dem Wasserbad gekocht, darauf im Va kuum der- grösste Teil des Alkohols abdestil- liert und der Rückstand mit 10 Teilen Wasser versetzt, dann die Lösung mit konz. Ammo niak gerade lackmusallialisch gestellt und vom Niederschlag abgesaugt. Nach Umkristallisie- ren desselben aus Wasser/Dioxan erhält man das Pyridin-4-aldehyd-thiosemicarbazon vom Smp. 232 bis 234 unter Zersetzung.
Claims (1)
- PATENTANSPRUCH: Verfahren zur Herstellung eines Thioseini- earbazons eines heterocyclischen Aldehyd, dadurch gekennzeichnet, dass man eine den Rest EMI0002.0035 abgebende Verbindung mit Hydrazin umsetzt und das erhaltene Hydrazon mit Rhodan- wasserstoffsäure behandelt. Die erhaltene neue Verbindung, das Pyri- din-4-aldehyd-thiosemicarbazon, zeigt. einen Smp. von 232 bis 234 .m <B>UNTERANSPRUCH:</B> Verfahren nach Patentansprueh, dadureli gekennzeichnet, dass man Pyridin-4-aldehyd finit Hydrazin umsetzt und das erhaltene Hydrazoll mit Rhodanwasserstoffsäure be handelt.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH288588T | 1950-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH288588A true CH288588A (de) | 1953-01-31 |
Family
ID=4486294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH288588D CH288588A (de) | 1950-08-09 | 1950-08-09 | Verfahren zur Herstellung eines Thiosemicarbazons eines heterocyclischen Aldehyds. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH288588A (de) |
-
1950
- 1950-08-09 CH CH288588D patent/CH288588A/de unknown
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