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, Facult¨¦ des Sciences Dhar El Mehraz, 50000 F¨¨s, Morocco.

b Laboratoire d¡¯Activation Mol¨¦culaire, Facult¨¦ des Sciences, 60000 Oujda, BP 524, Morocco.

e:-mail [email protected]

 

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

 

Keywords: Tridentate N Ligand - Pyrazole ¨C 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 ¡ãC.

 

IR (KBr, cm¨C1): 3262 (= C-H aromat); 3080 (CH); 1603 (C=C); 1500, 1472 (C=N); 1507; 1351; 1290; 1230.

 

1H-NMR (400 MHz, CDCl3): ¦Ä= 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 ¨C C5H7N2]+, 100%); 114 ([C5H7N2+NH4]+, 42.5%).

 

Acknowledgments

We are indebted to the "Programme Th¨¦matique d'Appui ¨¤ la Recherche Scientifique PROTARS N¡ã 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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