Molbank 2006, M465

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New bis-tridentate Nitrogen Ligand : N,N,N',N'-tetra-(3-carbomethoxy-5-methylpyrazol-1-ylmethyl)p-phenylenediamine

Maria DAOUDI,^a Brahim BENNANI,^a Assou ZAHIDI,^b Mohamed MCHICH,^b Taibi BEN HADDA^b,*

^a Laboratoire de Chimie Organique, Faculté des Sciences Dhar El Mehraz, 50000 Fès, Morocco.

^b Laboratoire d’Activation Moléculaire, Faculté des Sciences, 60000 Oujda, Morocco.

e-mail: [email protected]

Received: 15 July 2005 / Accepted: 6 September 2005 / Published: 28 February 2006

Keywords: bis-tridentate ligand - Pyrazole - Amine/ alcohol condensation - Electronic Communication.

The product 2 was prepared by the addition of p-phenylendiamine (NH₂C₆H₄NH₂) to 1 [1] according to the reported procedure [2]. To a solution of 1 (3.4 g, 20 mmol) in acetonitrile (45 ml) was added p-phenylendiamine (0.54 g, 5 mmol) and the mixture was stirred. The stirring was continued at room temperature for a week. The residue was precipitated by addition of cold water, purified and dried by hexane and under vacuum, to afford 2.63 g (74% yield) 2 as a white solid.

Melting Point: 197 °C.

IR (KBr, cm^–1): 3140 (=CH), 2990 (CH), 1730 (C=O), 1540 (C=C), 1480 (-C=N), 1450, 1410.

¹H-NMR (400 MHz, CDCl₃): δ= 7.25 (s, 4H, Ph); 6.5 (s, 4H, Pyrazol); 5.6 (s, 8H, N-CH₂-N); 4 (s, 12H, O-CH₃); 2.2 (s, 12H, CH₃). 

MS (m/z): 739 [M + Na⁺]; 716 [M]⁺; 613; 585; 460.

Acknowledgment:

We are indebted to the "Programme Thématique d'Appui à la Recherche Scientifique PROTARS N° P1T2/27", and the "Wylaya d'Oujda" for financial support.

References:

1. Dvoretzky, I.; Richter, G.H., J.Org.Chem., 1950, 15, 1285.

2. Sheu, S-C; Tien, M-J.; Cheng, M-C.; Ho, T-I.; Peng, S-M. And Lin, Y-C., J. Chem. Soc. Dalton Trans, 1995, 3503-3510.

Sample Availability: Available from the authors and MDPI.

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