(4-Metoksi-2-İyodofeniliminometil)-2-Nafton’ün Sentezi

Abstract

Bu çalışmada p-OCH₃ anilinden hazırlanan Schiff bazı (1), iyot sübstitüye Schiff bazını seniezlemek amacıyla DMSO, I₂, H₂S0₄ ile reaksiyona sokulmuştur. Reaksiyon DMSO, I₂, H₂S0₄’li ortamda 100°C’de, geri soğutucu ile ısıtarak gerçekleştirilmiştir. Reaksiyon ortamının pH’ı yaklaşık 5 olarak belirlenmiştir. pH’ı 2 civarında yapılan deneyde azometin (-CH=N-) bağınm kırıldığı tespit edilmiştir. Reaksiyon 100°C’de yaklaşık 14 saatlik sürede gerçekleştirilmiştir. Elde edilen ürünün (2) yapısı kütle, IR, UV, ¹³C-NMR, ¹H-NMR ve elementel analiz ile tayin edilmiştir. Reaksiyon koşullarında iyot, naftolik Schiff bazınm (1) fenil halkasına sübstitüye olmuştur.

In this study, Schiff base (1) which was prepared from 2-hydroxy-1-naphtaldehyde aniline and p-(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 DMSO, 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 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 14 hours. The structure of product was determined by mass, IR, UV, ¹³C-NMR, ¹H-NMR spectra and with elemental analysis. Under our reaction condition iodine was substituted to the phenyl ring of the naphtolic Schiff base (1).