DE574944C - Process for the preparation of 3, 4, 5-trisubstituted 1, 2, 4-triazoles - Google Patents

Process for the preparation of 3, 4, 5-trisubstituted 1, 2, 4-triazoles

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Publication number
DE574944C
DE574944C DESCH96856D DESC096856D DE574944C DE 574944 C DE574944 C DE 574944C DE SCH96856 D DESCH96856 D DE SCH96856D DE SC096856 D DESC096856 D DE SC096856D DE 574944 C DE574944 C DE 574944C
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triazoles
trisubstituted
preparation
dimethyl
reaction
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DESCH96856D
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German (de)
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Dr Robert Meyer
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Schering Kahlbaum AG
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Schering Kahlbaum AG
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Priority to DESCH96856D priority Critical patent/DE574944C/en
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Description

Verfahren zur Darstellung von 3, 4, 5 -trisubstituierten 1, 2, 4 -Triazolen Die Bildung von 1, 2, 4-Triazolen aus Hydrazidchlorfden mit Ammoniak und primären Aminen ist im Journal für praktische Chemie 73 [ igo6] , S. 279, beschrieben worden. Diese Methode versagt jedoch, sobald die beiden Acylreste nicht die gleichen sind (Journal für praktische Chemie 12o [i928], S.53).Process for the preparation of 3, 4, 5-trisubstituted 1, 2, 4 -triazoles The formation of 1, 2, 4-triazoles from hydrazide chlorides with ammonia and primary Amines has been described in the Journal for Practical Chemistry 73 [igo6], p. 279. However, this method fails as soon as the two acyl residues are not the same (Journal for practical chemistry 12o [1928], p.53).

Es wurde nun gefunden, daß man von Es ist bei dieser Reaktion belanglos, ob die Acylreste derselben Säure angehören oder nicht. Furodiazole reagieren sowohl mit aliphatischen und aromatischen wie auch mit heterocyclischen primären Aminen. Die Umsetzung des Brückensauerstoffes vollzieht sich auch in Lösungsmitteln, soweit diese die Reaktion nicht selbst stören. Die Anwendung von wasserentziehenden Mitteln kann die Reaktion nur günstig beeinflussen.It has now been found that In this reaction it is irrelevant whether the acyl radicals belong to the same acid or not. Furodiazoles react with aliphatic and aromatic as well as with heterocyclic primary amines. The conversion of the bridging oxygen also takes place in solvents as long as these do not themselves interfere with the reaction. The use of dehydrating agents can only have a beneficial effect on the reaction.

Die nach diesem Verfahren leicht zugänglichen substituierten Triazole sollen als Zwischenprodukte für pharmazeutische Präparate dienen. symmetrischen Diacylhydrazinen mit guten Ausbeuten zu substituierten 1,:2, 4-Triazolen gelangt, wenn man Diacylhydrazine nach bekannter Weise mit Phosphoroxychlorid in die entsprechenden Furodiazole überführt (Berichte der deutschen chemischen Gesellschaft 45 [igi2], S.282) und diese nun mit primären Aminen gemäß der Gleichung umsetzt Beispiel i 3, 4, 5-Trimethyl-i, 2, 4-triazol 11,5 g Dimethylfurodiazol (Journal für praktische Chemie 69 [1904], S. 151) werden einige Stunden mit 3o ccm der handelsüblichen 33°/oigen alkoholischen Methylaminlösung auf i io° erhitzt. Nach dem Abdestillieren der flüchtigen Anteile erstarrt das rückständige Öl beim Erkalten. Es werden 8,5 g des rohen Trimethyltriazols erhalten, das nach dem Umkristallisieren aus Wasser bei 94,5° schmilzt. Außer in Äther und Petroläther löst es sich leicht in den gewöhnlichen organischen Lösungsmitteln. Beispiel e 3, 5-Dimethyl-4-phenyltriazol Je 5 g Dimethylfurodiazol und Anilin werden i Stunde auf 14o° gehalten. Nach dem Erkalten werden aus dem Kristallbrei 5,6 g des Reaktionsproduktes abgesaugt. Das aus Essigestermethylalkoholumkristallisierte 3, 5-Dimethyl-4-phenyltriazol schmilzt bei 235°. Beispiel 3 3, 5-Dimethyl-4-phenetyltriazol io g Dimethylfurotriazol werden mit 149 Paraphenetidin 2 Stunden auf 1401 erhitzt. Aus dem erkalteten Reaktionsbrei werden die Kristalle abgesaugt, mit Äther gewaschen und aus Essigester umkristallisiert. Die Ausbeute an 3, 5-Dimethyl-4-phenetyltriazol beträgt 16g, F. 16i, 5 °.The substituted triazoles easily accessible by this process are intended to serve as intermediate products for pharmaceutical preparations. symmetrical Diacylhydrazines get substituted 1,: 2, 4-triazoles with good yields, if you diacylhydrazines in a known manner with phosphorus oxychloride in the corresponding Furodiazole transferred (reports of the German chemical society 45 [igi2], P.282) and now converts these with primary amines according to the equation Example i 3, 4, 5-trimethyl-i, 2, 4-triazole 11.5 g of dimethylfurodiazole (Journal for practical Chemie 69 [1904], p. 151) a few hours with 30 ccm of the commercially available 33% alcoholic methylamine solution heated to 10 °. After distilling off the volatile The remaining oil solidifies when it cools. There are 8.5 g of the crude trimethyltriazole obtained, which melts after recrystallization from water at 94.5 °. Except in Ether and petroleum ether dissolve easily in common organic solvents. example e 3, 5-dimethyl-4-phenyltriazole 5 g each of dimethylfurodiazole and aniline are added for one hour held at 14o °. After cooling, the crystal slurry becomes 5.6 g of the reaction product sucked off. The 3,5-dimethyl-4-phenyltriazole recrystallized from ethyl acetate methyl alcohol melts at 235 °. Example 3 3,5-Dimethyl-4-phenetyltriazole 10 g of dimethylfurotriazole are heated to 1401 with 149 paraphenetidine for 2 hours. From the cooled reaction pulp the crystals are suctioned off, washed with ether and recrystallized from ethyl acetate. The yield of 3,5-dimethyl-4-phenetyltriazole is 16 g, mp 16.5 °.

Beispiel 4 3. 5-nimethyl-4- (butyloxy-2) -pyr idyltriazol io g 2-Butyloxy-4-aminopyridin werden mit 5,9 g Dimethylfurodiazol 2 Stunden bei i50° verschmolzen. Die Aufarbeitung des Reaktionsproduktes geschieht wie im vorigen Beispiel und ergibt 4,5 g des 3, 5-Dimethyl-4-(butyloxy-2)-pyridyltriazols vom Schmelzpunkt 15q.,51. Beispiel s 3, 4-Dimethyl-5-phenyltriazol io g Methylphenylfurodiazol werden mit 30 ccm 33°/Qiger alkoholischer Methylaminlösung 4 Stunden auf 16o bis 17o° erhitzt. Der Rückstand der eingeengten Lösung wird mit verdünntem Alkali versetzt und in Benzol aufgenommen. Aus dem Benzolrückstand werden durch Umkristallisieren aus Essigester 5 g des 3, 4-Dimethyl-5-phenyltriazols vom Schmelzpunkt i37° erhalten.Example 4 3. 5-dimethyl-4- (butyloxy-2) -pyridyltriazole 10 g of 2-butyloxy-4-aminopyridine are fused with 5.9 g of dimethylfurodiazole at 150 ° for 2 hours. The reaction product is worked up as in the previous example and gives 4.5 g of 3,5-dimethyl-4- (butyloxy-2) -pyridyltriazole with a melting point of 15q., 51. Example s 3, 4-Dimethyl-5-phenyltriazole 10 g of methylphenylfurodiazole are heated to 16o to 17o ° for 4 hours with 30 cc of 33 ° / q alcoholic methylamine solution. The residue of the concentrated solution is mixed with dilute alkali and taken up in benzene. Recrystallization from ethyl acetate gives 5 g of 3,4-dimethyl-5-phenyltriazole with a melting point of i37 ° from the benzene residue.

Beispiel 6 3-Methyl-4, 5-diphenyltriazol 6,4 g Methylphenylfurodiazol werden mit 3,8 g Anilin i Stunde auf 140' gehalten. Aus dem nach dem Erkalten erstarrten Kristallbrei werden 2,6 g Reaktionsprodukt gewonnen, das aus verdünntem Methylalkohol gereinigt bei 1610 schmilzt.Example 6 3-methyl-4,5-diphenyltriazole 6.4 g of methylphenylfurodiazole are kept at 140 'for 1 hour with 3.8 g of aniline. From which froze after cooling Crystal slurry is obtained 2.6 g of the reaction product, which is obtained from dilute methyl alcohol purified at 1610 melts.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 3, 4, 5-trisubstituierten 1, 2, 4-Triazolen, dadurch gekennzeichnet, daB man 3, 5-substituierte Furodiazole mit primären aliphatischen, aromatischen oder heterocyclischen Aminen bei erhöhter Temperatur umsetzt.PATENT CLAIM: Process for the preparation of 3, 4, 5-trisubstituted 1,2,4-Triazoles, characterized in that 3,5-substituted furodiazoles are used with primary aliphatic, aromatic or heterocyclic amines at increased Temperature converts.
DESCH96856D 1932-02-14 1932-02-14 Process for the preparation of 3, 4, 5-trisubstituted 1, 2, 4-triazoles Expired DE574944C (en)

Priority Applications (1)

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DESCH96856D DE574944C (en) 1932-02-14 1932-02-14 Process for the preparation of 3, 4, 5-trisubstituted 1, 2, 4-triazoles

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Application Number Priority Date Filing Date Title
DESCH96856D DE574944C (en) 1932-02-14 1932-02-14 Process for the preparation of 3, 4, 5-trisubstituted 1, 2, 4-triazoles

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004037809A1 (en) * 2002-10-25 2004-05-06 Pfizer Limited Triazole compounds for the treatment of dysmenorrhoea
US7084145B2 (en) 2002-10-25 2006-08-01 Pfizer Inc. Triazole compounds useful in therapy

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004037809A1 (en) * 2002-10-25 2004-05-06 Pfizer Limited Triazole compounds for the treatment of dysmenorrhoea
US7084145B2 (en) 2002-10-25 2006-08-01 Pfizer Inc. Triazole compounds useful in therapy

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