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

Year 2023, Volume: 27 Issue: 2, 291 - 296, 25.08.2023

Melek Gökmen Karakaya

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

Supporting Institution

UŞAK ÜNİVERSİTESİ

Project Number

2015/MF008 CLİMBAZOLE VE METRONİDAZOLE TÜREVLERİNİN SENTEZİ

Thanks

UŞAK ÜNİVERSİTESİ PROF. DR. ABDULLAH MENZEK (ATATÜRK ÜNİVERSİTESİ)

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

Project Number

2015/MF008 CLİMBAZOLE VE METRONİDAZOLE TÜREVLERİNİN SENTEZİ

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