DE953802C - Process for the preparation of a pyridine derivative - Google Patents
Process for the preparation of a pyridine derivativeInfo
- Publication number
- DE953802C DE953802C DEF14613A DEF0014613A DE953802C DE 953802 C DE953802 C DE 953802C DE F14613 A DEF14613 A DE F14613A DE F0014613 A DEF0014613 A DE F0014613A DE 953802 C DE953802 C DE 953802C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- pyridine derivative
- parts
- mercapto
- pyridyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
AUSGEGEBEN AM 6. DEZEMBER 1956ISSUED DECEMBER 6, 1956
JYr. 953 802 KLASSE 12p GRUPPE 10 INTERNAT. KLASSE C07d JYr. 953 802 CLASS 12p GROUP 10 INTERNAT. CLASS C07d
Dr. Hans-Bodo König, Wuppertal-Elberfeld, und Dr. Hans-Albert Offe, Wuppertal-ElberfeldDr. Hans-Bodo König, Wuppertal-Elberfeld, and Dr. Hans-Albert Offe, Wuppertal-Elberfeld
sind als Erfinder genannt wordenhave been named as inventors
Farbenfabriken Bayer Aktiengesellschaft, Leyerkusen-BayerwerkPaint factories Bayer Aktiengesellschaft, Leyerkusen-Bayerwerk
Verfahren zur Herstellung eines PyridinderivatesProcess for the preparation of a pyridine derivative
Patentiert im Gebiet der Bundesrepublik Deutschland vom 4, Mai 1964 anPatented in the territory of the Federal Republic of Germany on May 4, 1964
Patentanmeldung bekanntgemacnt am. 14. Juni 1956 Patenterteilung bekanntgemacht am 15. November 1956Patent application announced on June 14, 1956 Patent issued November 15, 1956
Es wurde gefunden, daß man ein neues Pyridinderivat erhält, dem die Konstitution eines 3-Mercapto-4-amino-5-(γ-pyridyl) -1, 2, 4-triazole oder' eines 3 - Mercapto - 6 - (γ - pyridyl) -1, 2 - dihydro ι, 2, 4; 5~tetrazins zukommt, wenn man Alkalisalze der Dithioisonicotinsäure mitThiocarbohydrazid inIt has been found that a new pyridine derivative is obtained which has the constitution of a 3-mercapto-4-amino-5- (γ- pyridyl) -1, 2, 4-triazole or a 3 - mercapto - 6 - (γ - pyridyl) -1, 2 - dihydro ι, 2, 4; 5 ~ trazins te belongs when alkali metal salts of Dithioisonicotinsäure mitThiocarbohydrazid in
Gegenwart von alkalisch reagierenden Stoffen umsetzt. Reacts the presence of alkaline substances.
Die Reaktion, die dem Verfahren gemäß vorliegender Erfindung zugrunde liegt, kann folgendermaßen formuliert werden: . .The reaction underlying the method of the present invention can be carried out as follows be formulated:. .
NH2 NH 2
/ ■ v / ■ v
C C — SH oderC C - SH or
NH2 NH 2
N^-NN ^ -N
/ ■ ■ v / ■ ■ v
C C-SHC C-SH
XNH-NHX X NH-NH X
NH2 NH 2
Die Darstellung der als Ausgangsmaterial dienenden Alkalisalze der Dithioisonicotinsäure ist in den Chem. Ber. 87, 829 (1954) beschrieben.The representation of the alkali metal salts of dithioisonicotinic acid used as starting material is in the Chem. Ber. 87, 829 (1954).
Das neue Verfahren wird zweckmäßig in wäßriger Lösung ausgeführt. Dabei kann man z. B. so verfahren, daß man die Ausgangsstoffe, dithioisonicotinsaures Alkali und Thiocarbohydrazid, nach Zusatz von Alkalicarbonat als Kondensationsmittel einige Stunden in wäßriger Lösung am Rückfluß erhitzt. Zur Aufarbeitung wird mit Mineralsäure neutralisiert, gekühlt und das erhaltene rohe s-Mercapto-^z-amino-S-fy-pyridyl)-]:, 2, 4-triazol abfiltriert.The new process is expediently carried out in aqueous solution. You can z. B. proceed in such a way that the starting materials, alkali dithioisonicotinic acid and thiocarbohydrazide, after the addition of alkali carbonate as a condensing agent for a few hours in aqueous solution Heated to reflux. For work-up, it is neutralized with mineral acid, cooled and the resulting product crude s-mercapto- ^ z-amino-S-fy-pyridyl) -] :, 2, 4-triazole filtered off.
Das durch die Erfindung zugänglich gewordene 3-Mercapto-4-amino-5-(y-pyridyl)-i, 2,4-triazol soll als Heilmittel und als Zwischenprodukt für die Herstellung von Heilmitteln Verwendung finden.The 3-mercapto-4-amino-5- (y-pyridyl) -i, 2,4-triazole made accessible by the invention should as a remedy and as an intermediate for the manufacture of remedies use.
10 Gewichtsteile dithioisonicotinsaures Kalium, 6,8 Gewichtsteile Thiocarbohydrazid, 6 Gewichtsteile wasserfreies Kaliumcarbonat und 300 Volumteile Wasser werden 6 bis 7 Stunden unter Rückfluß gekocht, die Reaktionslösung nach dem Erkalten mit io°/oiger Salzsäure neutralisiert, in Eis gekühlt, der ausgefallene rötlich-weiße Niederschlag abgesaugt, mit Wasser gewaschen, getrocknet und aus siedendem Alkohol umkristallisiert. 10 parts by weight of potassium dithioisonicotinate, 6.8 parts by weight of thiocarbohydrazide, 6 parts by weight of anhydrous potassium carbonate and 300 parts by volume Water is refluxed for 6 to 7 hours, the reaction solution after cooling Neutralized with 10% hydrochloric acid, cooled in ice, the resulting reddish-white precipitate Sucked off, washed with water, dried and recrystallized from boiling alcohol.
Ausbeute 5,2 Gewichtsteile (52% der Theorie). Schmp. Zers. ab etwa 2400 (Koflerbank, korr.).Yield 5.2 parts by weight (52% of theory). M.p. dec. from about 240 0 (Koflerbank, corr.).
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF14613A DE953802C (en) | 1954-05-04 | 1954-05-04 | Process for the preparation of a pyridine derivative |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US427647A US2776282A (en) | 1954-05-04 | 1954-05-04 | Cyclic amides of alpha-toluic acids and derivatives thereof |
DEF14613A DE953802C (en) | 1954-05-04 | 1954-05-04 | Process for the preparation of a pyridine derivative |
Publications (1)
Publication Number | Publication Date |
---|---|
DE953802C true DE953802C (en) | 1956-12-06 |
Family
ID=25973889
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF14613A Expired DE953802C (en) | 1954-05-04 | 1954-05-04 | Process for the preparation of a pyridine derivative |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE953802C (en) |
-
1954
- 1954-05-04 DE DEF14613A patent/DE953802C/en not_active Expired
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