DE899193C - Process for the preparation of imidazole derivatives - Google Patents

Process for the preparation of imidazole derivatives

Info

Publication number
DE899193C
DE899193C DEB16616A DEB0016616A DE899193C DE 899193 C DE899193 C DE 899193C DE B16616 A DEB16616 A DE B16616A DE B0016616 A DEB0016616 A DE B0016616A DE 899193 C DE899193 C DE 899193C
Authority
DE
Germany
Prior art keywords
vinyl
imidazole derivatives
preparation
formaldehyde
methylimidazole
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
DEB16616A
Other languages
German (de)
Inventor
Dr Curt Schuster
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DEB16616A priority Critical patent/DE899193C/en
Application granted granted Critical
Publication of DE899193C publication Critical patent/DE899193C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

Verfahren zur Herstellung von Imidazolderivaten Gegenstand des Patentes 882 7o2 ist ein Verfahren zur Herstellung von Imidazolderivaten, bei dem man N-Vinylimidazolverbindungen, die am C-Atom 2 ein Wasserstoffatom enthalten, mit Aldehyden umsetzt.Process for the preparation of imidazole derivatives the subject of the patent 882 7o2 is a process for the production of imidazole derivatives, in which N-vinylimidazole compounds, which contain a hydrogen atom at C atom 2, reacts with aldehydes.

Es wurde nun gefunden, daB man ebenfalls wertvolle oxygruppenhaltige Kondensationsprodukte herstellen kann, wenn man N-Vinylimidazole, die am C-Atom 2 eine Methylgruppe tragen, mit Aldehyden, vorzugsweise Formaldehyd, oder aldehydabspaltenden Stoffen umsetzt.It has now been found that valuable oxy groups are also found Can produce condensation products if you have N-vinylimidazoles, which are on the carbon atom 2 carry a methyl group, with aldehydes, preferably formaldehyde, or aldehyde-releasing agents Implements substances.

Bei Einwirkung von Formaldehyd auf N-Vinyl-2-methylimidazol verläuft die Umsetzung offenbar unter Bildung des N-Vinyl-2-oxäthylimidazols nach folgendem Schema: Für das Verfahren geeignete N-Vinylimidazole mit einer Methylgruppe am C-Atom 2 sind außer N-Vinyl-2-methylimidazol z. B. N-Vinyl-2-methylbenzimidazol, N-Vinyl-2-methylnaphthimidazol und deren Substitutionsprodukte.When formaldehyde acts on N-vinyl-2-methylimidazole, the reaction evidently proceeds with formation of N-vinyl-2-oxethylimidazole according to the following scheme: For the process suitable N-vinylimidazoles with a methyl group on C atom 2 are in addition to N-vinyl-2-methylimidazole z. B. N-vinyl-2-methylbenzimidazole, N-vinyl-2-methylnaphthimidazole and their substitution products.

Die Umsetzung wird zweckmäßig in wäßriger oder alkoholischer Lösung durch Erwärmen unter Rückflußkühlung oder in geschlossenen Gefäßen vorgenommen. Die günstigsten Reaktionstemperaturen liegen zwischen 4o und i40°, vorzugsweise zwischen 70 und iio°. Die Umsetzungsprodukte können z. B. durch - Abdampfen des überschüssigen Formaldehyds und des Lösungsmittels isoliert und durch Vakuumdestillation gereinigt werden.The reaction is expediently carried out in an aqueous or alcoholic solution by heating under reflux cooling or in closed vessels. The most favorable reaction temperatures are between 40 and 140 °, preferably between 70 and 110 °. The reaction products can, for. B. isolated by evaporation of the excess formaldehyde and the solvent and purified by vacuum distillation.

Die neuen Kondensationsprodukte sind infolge der Anwesenheit einer Vinylgruppe und einer reaktionsfähigen Oxygruppe zu mannigfachen Umsetzungen befähigt und können beispielsweise als Zwischenprodukte für die Herstellung von Heilmitteln verwendet werden. Beispiel 5o Teile N-Vinyl-2-methylimidazol werden mit ioo Teilen 3o°/oigem Formaldehyd in einem geschlossenen Gefäß io Stunden auf ioo° erhitzt. Das Reaktionsgemisch wird im Vakuum eingeengt und nach Entfernung des überschüssigen Formaldehyds und des Wassers im Vakuum destilliert. Bei 2o mm/Hg Druck und 170 bis i72° destillieren etwa 5o Teile N-Vinyl-2-oxäthylimidazol als farblose Flüssigkeit über. Als Vorlauf erhält man bei der Destillation etwas unverändertes N-Vinyl-2-rnethylimidazol.The new condensation products are due to the presence of a Vinyl group and a reactive oxy group capable of diverse reactions and can be used, for example, as intermediates for the manufacture of medicinal products be used. Example 50 parts of N-vinyl-2-methylimidazole are mixed with 100 parts 30% formaldehyde in a closed vessel heated to 100 ° for 10 hours. The reaction mixture is concentrated in vacuo and, after removing the excess Formaldehyde and water distilled in vacuo. At 2o mm / Hg pressure and 170 to About 50 parts of N-vinyl-2-oxethylimidazole distilled at i72 ° as a colorless liquid above. Somewhat unchanged N-vinyl-2-methylimidazole is obtained as the first runnings in the distillation.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Imidazolderivat en nach dem Patent 882 702, dadurch gekennzeichnet, daß man N-Vinylimidazole, die am C-Atom 2 eine Methylgruppe enthalten, mit Aldehyden, vorzugsweise Formaldehyd, umsetzt. PATENT CLAIM: Process for the production of imidazole derivatives according to patent 882 702, characterized in that N-vinylimidazoles which contain a methyl group on carbon atom 2 are reacted with aldehydes, preferably formaldehyde.
DEB16616A 1951-09-05 1951-09-05 Process for the preparation of imidazole derivatives Expired DE899193C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB16616A DE899193C (en) 1951-09-05 1951-09-05 Process for the preparation of imidazole derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB16616A DE899193C (en) 1951-09-05 1951-09-05 Process for the preparation of imidazole derivatives

Publications (1)

Publication Number Publication Date
DE899193C true DE899193C (en) 1953-12-10

Family

ID=6958988

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB16616A Expired DE899193C (en) 1951-09-05 1951-09-05 Process for the preparation of imidazole derivatives

Country Status (1)

Country Link
DE (1) DE899193C (en)

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