The Synthesis of 1-(N-2’-Iodo-5,-Methoxyphenyuminomethyl)-2-Naphtol and (1-N-2’,4’- Diiodo-5'-Methoxyphenyliminomethyl)-2-Naphtol

Abstract

In this study, Schiff base (1) which was prepared from 2-hydroxy-1-naphtaldéhyde aniline and m-(methoxy) substituted aniline were reacted with DMSO, I₂,H₂S0₄ in the hope of preparing Schiff base which was substituted with iodine . The reaction has been carried out with DMS0-I₂-H₂S0₄ at 100°C under atmospheric conditions. Reaction has been followed with TLC and the pH of the reactions medium were approximately at 5. In the experiment was carried out approximately at pH ≡ 2 the azomethine (-CH=N-) bond breaking was found . The reaction of the naphtolic Schiff base (1) with DMSO-I₂-H₂S0₄ was carried out at 100°C for about 10 hours. The structure of product was determined by mass, IR, UV, ¹H-NMR, ¹³C-NMR spectra and with elemental analysis. Under our reaction condition iodine was substituted to the phenyl ring of the naphtolic Schiff base (1).

Bu çalışmada m-OCH₃ anilinden hazırlanan Schiff bazı (1) ile, iyot sübstitüye Schiff bazını sentezlemek amacıyla ; DMSO, I₂, H₂S0₄ ile reaksiyona sokulmuştur. Reaksiyon DMSO, I₂, H₂S0₄'li ortamda 100°C'de, geri soğutucu altında gerçekleştirilmiştir. Reaksiyon ortamının pH'ı yaklaşık 5 olarak belirlenmiştir. pH'ı 2 civarında yapılan deneyde azometin (-CH=N-) bağının kırıldığı tespit edilmiştir. Reaksiyon 100°C'de yaklaşık 10 saatlik sürede gerçekleştirilmiştir. İzole ürünlerin (2,3) yapısı kütle, IR, UV, ¹³C-NMR, ¹H-NMR ve elementel analiz ile tayin edilmiştir. Reaksiyon koşullarında iyot, naftolik Schiff bazının (1) fenil halkasına sübstitüye olmuştur.