The synthesis of 1-(N-2'-IODO-5'-methoxyphenyliminomethyl)-2-naphtol and (1-N-2',4'-diiodo-5'-methoxyphenyliminomethyl)-2-naphtol

1-(N-2'-iyodo-5'-metoksifeniliminometil)-2-naftol ve 1-(N-2',4'-diiyodo-5'-metoksifeniliminometil)-2-naftol' ün sentezi

Özet

Bu çalışmada m-OCH3 anilinden hazırlanan Schiff bazı (1) ile, iyot sübstitüye Schiff bazını sentezlemek amacıyla ; DMSO, I2, H2SO4 ile reaksiyona sokulmuştur. Reaksiyon DMSO, I2, H2SO4'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=NN-) 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.

Abstract

In this study, Schiff base (1) which was prepared from 2-hydroxy-l-naphtaldehyde aniline and m-(methoxy) substituted aniline were reacted with DMSO, I2,H2SO4 in the hope of preparing Schiff base which was substituted with iodine . The reaction has been carried out with DMSO-I2-H2SO4 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 $pHwidetilde{=}2$ the azomethine (-CH=N-) bond breaking was found . The reaction of the naphtolic Schiff base (1) with DMSO-I2-H2SO4 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).