A Different Method for Synthesis of 2-(2-Methyl-5-nitro-1H-imidazol-1-yl)acetaldehyde

Abstract

Metronidazole was discovered for the first time in 1959 at the Rhone Poulanc Research laboratory in France. It is an antibiotic and antiprotozoal drug active substance, which is on the World Health Organization's list of essential drugs. It has been shown by the studies carried out since 1975 that metronidazole was oxidized to the related aldehyde or further oxidized to the related acid by the bacteria in the human body and in the research laboratories by various methods. Many scientists have published many articles, containing schiff base synthesis, oxime formation and reductive amination reactions, using as a reactive substance aldehyde, the subject of this article. The oxidation of metronidazole is important for aquatic environments. On this subject, various computational and experimental studies are available in the literature in order to treat wastewater with various oxidation methods. In this study, 2-(2-methyl-5-nitro-1H-imidazol-1- yl)acetaldehyde was obtained by the controlled oxidation reaction method which was different from the literature. In this method in a round bottom flask, equal equivalent metronidazole and pyridinium chlorochromate were solved in dichloromethane. The solution was stirred magnetically for 24 hours at room temperature. The crude product contains approximately half-and-half unreacted metronidazole and the product aldehyde. The product was purified by TLC method for 1H-NMR, FTIR spectroscopic analysis and melting point determination.

Keywords

• 2-(2-methyl-5-nitro1H-imidazol-1-yl) acetaldehyde
• Metronidazole
• Oxidation
• FTIR
• NMR
• TLC

Farklı Bir Yöntemle 2-(2-Metil-5-nitro-1H-imidazol-1-il)asetaldehit Eldesi

Abstract

Metronidazol Dünya Sağlık Örgütünün temel ilaçlar listesinde yer alan ilk defa 1959 yılında Fransa'da Rhone Poulanc Araştırma laboratuvarında keşfedilen antibiyotik ve antiprotozoal ilaç etkin maddesidir. Metronidazolün insan vücudunda bulunan bakteriler tarafından ve araştırma laboratuvarlarında çeşitli metotlarla kontrollü olarak yükseltgenerek ilgili aldehite veya daha da yükseltgenerek ilgili asite yükseltgendiği 1975 yılından günümüze yayınlanan çalışmalarda gösterilmiştir. Birçok bilim insanı makalenin konusu aldehiti reaktif olarak kullanarak schiff bazı eldesi, oksim oluşumu ve redüktif aminasyon reaksiyonlarını yayınlamıştır. Metronidazolün yükseltgenmesi sucul ortamlar için önemlidir. Atık sulardaki metronidazolün arıtılması amacıyla, çeşitli yöntemlerle metronidazolün yükseltgenmesi için hesaplamalı ve deneysel çalışmalar literatürde mevcuttur. Bu çalışmada, literatürden farklı bir yöntemle 2-(2-metil-5-nitro-1H-imidazol-1- il)asetaldehit, metronidazolün kontrollü yükseltgenmesi reaksiyonu ile elde edilmiştir. Bu reaksiyon, dibi yuvarlak bir reaksiyon balonunda oda sıcaklığında eşit ekivalentlerde metronidazol ve piridinyum klorokromatın diklorometan içindeki çözeltisinin 24 saat manyetik olarak karıştırılmasıyla gerçekleştirilmiştir. Yükseltgenme reaksiyonu sonucunda elde edilen ham ürün yaklaşık yarı yarıya reaksiyona girmemiş metronidazolü ve yükseltgenmiş ürün aldehiti içermektedir. Ürünün 1H-NMR, FTIR spektroskopik analizleri ve erime noktası tayini amacıyla saflaştırılması için İTK yöntemi kullanılmıştır.

Keywords

• 2-(2-Metil-5-nitro1H-imidazol-1-il) asetaldehit
• Metronidazol
• Yükseltgeme
• FTIR
• NMR
• İTK

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