DE953802C - Process for the preparation of a pyridine derivative - Google Patents

Process for the preparation of a pyridine derivative

Info

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
Application number
DEF14613A
Other languages
German (de)
Inventor
Dr Hans-Bodo Koenig
Dr Hans-Albert Offe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to DEF14613A priority Critical patent/DE953802C/en
Priority claimed from US427647A external-priority patent/US2776282A/en
Application granted granted Critical
Publication of DE953802C publication Critical patent/DE953802C/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/16Heterocyclic 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
    • C07D295/18Heterocyclic 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
    • C07D295/182Radicals derived from carboxylic acids
    • C07D295/185Radicals 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

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

AUSGEGEBEN AM 6. DEZEMBER 1956ISSUED DECEMBER 6, 1956

DEUTSCHES PATENTAMTGERMAN PATENT OFFICE PATENTSCHRIFTPATENT LETTERING

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.

Beispielexample

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)

PATENTANSPRUCH:PATENT CLAIM: Verfahren zur Herstellung eines Pyridinderivates, dadurch gekennzeichnet, daß man Alkalisalze der Dithioisonicotinsäure mit Thiocarbohydrazid in Gegenwart alkalisch reagierender Stoffe, zweckmäßig in wäßriger Lösung, umsetzt.Process for the preparation of a pyridine derivative, characterized in that one Alkali salts of dithioisonicotinic acid with thiocarbohydrazide in the presence of alkaline reactants Substances, expediently in aqueous solution, implemented. θ 609530/455 6.56 (609 701 U. 56)θ 609530/455 6.56 (609 701 U. 56)
DEF14613A 1954-05-04 1954-05-04 Process for the preparation of a pyridine derivative Expired DE953802C (en)

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)

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