Molbank 2006, M483

N,N-bis[(1,5-dimethylpyrazol-3-yl)methyl]para-toluidine

Ibrahim Bouabdallah*, Abdelkrim Ramdani, Ismail Zidane and Rachid Touzani

Laboratoire de Chimie Organique Physique, Département de Chimie, Faculté des Sciences, Université Mohamed Premier, BP 524, 60000, Oujda, Maroc

e-mail: [email protected]

*Author to whom correspondence should be addressed

Received: 24 October 2005 / Accepted: 15 January 2006 / Published: 1 June 2006

Keywords : Tripod, pyrazol, ligand, tridentate.

The mixture of para-toluidine 1 (0.535 g, 5 mmol), 3-chloromethyl-1,5-dimethylpyrazol 2 (1.44 g, 10 mmol) and sodium carbonate (4.24 g, 40 mmol) in acetonitrile (50 mL) was refluxed for three hours [1, 2, 3]. The solvent was removed at reduced pressure. The residue was purified through a silica column (CH₂Cl₂) to give the product 3 (726 mg, 45 % yield) as a white solid.

Melting point: 98 - 100°C (CCl₄)

IR (KBr, cm^-1): 3020 (ν_=C-H); 2960 (ν_{C-H, CH3}); 2920 (ν_{C-H, CH2}); 2875 (ν_{C-H, N-CH3}); 1620 (ν_C=N); 1530 (ν_C=C); 1430; 1390 (δ_C-N); 1340; 1235; 1185; 940; 800 (δ_=C-H); 780.

¹H-NMR (CDCl₃, 300 MHz): d= 6.94 (d, 2 H, H2’, J = 8.4 Hz); 6.78 (d, 2 H, H3’, J = 8.4 Hz); 5.85 (s, 2 H, C4-H); 4.46 (s, 4 H, N-CH₂-pz); 3.69 (s, 6 H, N-CH₃); 2.19 (s, 3 H, CH₃-C₆H₄); 2.16 (s, 6 H, C5-CH₃).

¹³C-NMR (CDCl₃, 75 MHz): d= 149.72 (C3); 143.50 (C1’); 139.51(C5); 129.85 (C3’); 125.42 (C4’); 113.54 (C2’); 104.51(C4); 49.34 (N-CH2-pz); 36.25 (N-CH3); 20.62 (CH₃-C₆H₄); 11.65 (C5-CH₃).

MS (EI), m/z: 323 (5.4 %); 228 (0.4 %); 214 (100 %); 109 (24.5 %); 91 (4.4 %); 77 (0.5 %); 56 (4.9 %); 40 (3.5 %).

References and Notes:

1. Bouabdallah, I.; Ramdani, A. ; Zidane, I. and Touzani, R. Molbank, 2005, M 397.

2. Bouabdallah, I.; Ramdani, A. ; Zidane, I. ; Touzani, R.; Eddike, D.; Radi, S. and Haidoux, A. J. Chem. Res., 2005, April, 242 - 244.

3. Malek, F. Thèse de Doctorat d’Etat, Faculté des Sciences, Oujda, Maroc, 1995.

Sample Availability: Available from MDPI.