Molbank 2006, M466

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Synthesis of tridentate Nitrogen Ligand : N,N-bis-(3,5-dimethylpyrazol-1-ylmethyl)benzylamine (NNNN)

Maria DAOUDI,^a Brahim BENNANI,^a Assou ZAHID,^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, BP 524, Morocco.

e:-mail benhadda@sciences.univ-oujda.ac.ma

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

Keywords: Tridentate N Ligand - Pyrazole – Amine/ alcohol condensation.

The product 2 was prepared by the addition of benzylamine (C₆H₅CH₂NH₂) to 1 [1] according to the reported procedure [2]. To a solution of 1 (1.26 g, 10 mmol) in acetonitrile (25 ml) was added benzylamine (0.536 g, 5 mmol) and the mixture was stirred. The stirring was continued at room temperature for 4 days. The residue was precipitated by addition of cold water, purified and dried by hexane and under vacuum, to afford 2 as a white solid (1.08 g, 63%).

Melting point: 72 °C.

IR (KBr, cm^–1): 3262 (= C-H aromat); 3080 (CH); 1603 (C=C); 1500, 1472 (C=N); 1507; 1351; 1290; 1230.

¹H-NMR (400 MHz, CDCl₃): δ= 7.4 (s, 5H, Ph); 5.9 (s, 2H, Pyrazol); 5 (s, NCH₂N); 3.9 (s, 2H, Ph-CH₂-N); 2.3 (s, 6H, CH₃); 2.1 (s, 6H, CH₃).

MS (DCI/NH₃, CHCl₃) = Calculated for [M]⁺, C₁₉H₂₅N₅= 323. Found 324 ([M+H]⁺, 92.5%); 228 ([MH – C₅H₇N₂]⁺, 100%); 114 ([C₅H₇N₂+NH4]⁺, 42.5%).

Acknowledgments

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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