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Volume 2004
Issue 1
10.3390/M358
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Short Note

Synthesis of novel Schiff base N-[(E)-1-(1H-indole-3-yl)methylidene]-N-[4-(4-{[(E)-1-(1H-indol-3-yl)methylidene]amino} phenoxy)phenyl] amine

by
A. A. Jarrahpour
* and
M. Zarei
Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
*
Author to whom correspondence should be addressed.
Molbank 2004, 2004(1), M358; https://doi.org/10.3390/M358
Submission received: 23 August 2003 / Accepted: 11 February 2004 / Published: 24 February 2004
Versions Notes
Molbank 2004 m358 i001
A mixture of 4,4'-diaminodiphenyl ether 1 (2.00 g, 10.00 mmol), indole-3-carboxaldehyde 2 (2.90 g, 20.00 mmol) in absolute ethanol (50.00 mL) was stirred at room temperature for 8 hours. Then the solvent was evaporated under reduced pressure to give the crude imine as a solid . The new Schiff base 3 was recrystallized from methanol (3.25 g, 71%).
m.p. 252-254 oC.
IR (KBr) (cm-1): 1624 (C=N), 3424 (NH )
1H-NMR (DMSO) (250 MHz)δ(ppm): 7.05-7.99 (16H, m, 4Ph), 8.37 (2H, d, C=CH), 8.74 (2H, s, N=CH), 11.76 (2H, br , indole NH)
13C-NMR (DMSO) (62.90 MHz)δ(ppm): 112.3-137.5 (aromatic carbons), 148.98 (C=CHNH), 155.18 (C=N)
MS (m/z, %): 454 (M + ,9.10), 325 (InC=NphOPhN, 40.00 ), 235 (InC=NPhO, 100.00), 117 (In, 20.00), 92 (PhO, 10.00), 90 (PhN, 8.30), 76 (PhH)

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

The authors thank the Shiraz University Research Council for financial support (Grant No. 81-SC-1495-C191).
  • Sample availability: Available from MDPI

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MDPI and ACS Style

Jarrahpour, A.A.; Zarei, M. Synthesis of novel Schiff base N-[(E)-1-(1H-indole-3-yl)methylidene]-N-[4-(4-{[(E)-1-(1H-indol-3-yl)methylidene]amino} phenoxy)phenyl] amine. Molbank 2004, 2004, M358. https://doi.org/10.3390/M358

AMA Style

Jarrahpour AA, Zarei M. Synthesis of novel Schiff base N-[(E)-1-(1H-indole-3-yl)methylidene]-N-[4-(4-{[(E)-1-(1H-indol-3-yl)methylidene]amino} phenoxy)phenyl] amine. Molbank. 2004; 2004(1):M358. https://doi.org/10.3390/M358

Chicago/Turabian Style

Jarrahpour, A. A., and M. Zarei. 2004. "Synthesis of novel Schiff base N-[(E)-1-(1H-indole-3-yl)methylidene]-N-[4-(4-{[(E)-1-(1H-indol-3-yl)methylidene]amino} phenoxy)phenyl] amine" Molbank 2004, no. 1: M358. https://doi.org/10.3390/M358

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