Synthesis of 2-({[4-(4-{[(E)-1-(2-hydroxy-3-methoxyphenyl) methylidene]amino}phenoxy)phenyl]imino}methyl)- 6 -methoxy phenol

A. A. jarrahpour*, M. Zarei

Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran Tel. No. 0098 711 2284822,  Fax: 0098 711 2280926, E-mail: [email protected],  [email protected]

Received: 20 July 2003 / Accepted: 18 September 2003 / Published: 24 February 2004

A mixture of  4,4'-diaminodiphenyl ether 1 (1.00 g, 5.00 mmol), o-vanillin 2 (1.52 g , 10.00 mmol) in methanol  (40.00 mL) was stirred at room temperature for one hour to give an orange precipitate.Then it was filtered and washed with methanol to give the pure imine 3 (2.27 g, 97.00 %).

m.p. 134-136 ^oC.

IR (KBr) (cm^-1): 1620.4(C=N), 3050-3300 (OH)

¹H-NMR (DMSO) (250 MHz) (ppm): 3.87 (6H, s, 2OCH₃), 6.59-7.40 (14H, m, 4Ph), 8.59 (2H, s,  N=CH), 13.61 (2H, s, OH)

¹³C- NMR (DMSO) (62.90 MHz) (ppm): 56.60 (OCH₃), 115.29-134.1 (aromatic carbons), 161.96 (C=N) 

MS (m/z, %): 468(M⁺, 21.5), 406 (HOPh(O)C=NPhOPHN=CPh), 17.5), 242 (CH₃OPhOHC=NPh(O), 6), 150 (CH₃OPhOHC=N, 18.7), 136 (CH₃OPhOHCH, 6.3) ,123 (CH₃OPhOH, 10), 119(Ph(O)N=CH, 5.1), 76 (PhH), 43 (C-OCH₃, 100), 41 (C=C-OH, 94).

Acknowledgment

The authors thank the Shiraz University Research Council for financial support (Grant No. 81-SC-1540-C220 ).

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