Molbank 2005, M397

http://www.mdpi.net/molbank/

 

N,N-bis[3-(1,5-dimethylpyrazolyl)methyl]aniline

 

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

 

Laboratoire de Chimie Organique Physique, Département de Chimie, Faculté des Sciences,

Université Mohamed Premier, BP 524, 60000, Oujda , Maroc,

e-mail : [email protected]. [email protected].

 

Received: 18 March 2004 / Accepted: 25 March 2004 / Published: 1 July 2005

 

Keywords: pyrazol, ligand.

 


 

The mixture of aniline 1 (97 mg, 1 mmol), 3-chloromethyl-1,5-dimethyl pyrazol 2 (301.6 mg, 2 mmol)  and sodium carbonate (444 mg, 4 mmol) in acetonitrile (10 mL) was refluxed for three hours [1, 2]. The solvent was removed at reduced pressure. The residue was purified by recrystallysation to afford the produt 3 as a white solid. Yield: (205 mg, 69 %).

 

Melting point: 132-134°C (CH2Cl2).

 

IR (KBr, cm-1):  2930 (CH3); 1586 (C=C); 1500 (C=N); 1390, 1260, 1180, 1030, 990, 880.

 

1H-NMR (300 MHz, CDCl3)  : δ= 7.14 (t, 2H, H2, J = 7.27 Hz) ;  6.87 (d, 2H, H1, J = 8.32 Hz) ;  6.64 (t, 1H, H3, J = 7.27 Hz); 5.86 (s, 2H, C-H pyrazol); 4.49 (s, 4H, N-CH2);  3.70 (s, 6H, N-CH3 ); 2.16 ( s, 6H, CH3).

 

13C-NMR (75 MHz, CDCl3): δ= 139.56; 129.32; 113.27; 104.50; 49.08; 36.25; 11.63.

 

EI-MS (70 eV, m/z): 309; 200; 109; 95; 77; 56.

 

References and Notes:

1. Driessen, W. J. R. Neth. Chem. Soc. 1982, 101, 441.

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

 

Sample Availability: Available from the Authors.

 

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