BenzenaMine, 4-(4,5-dihydro-1H-iMidazol-2-yl)- synthesis
- Product Name:BenzenaMine, 4-(4,5-dihydro-1H-iMidazol-2-yl)-
- CAS Number:61033-71-4
- Molecular formula:C9H11N3
- Molecular Weight:161.2
Yield:61033-71-4 84%
Reaction Conditions:
with [Ru(CO)(pyridoxal thiosemicarbazone hydrochloride)(AsPh3)2] in neat (no solvent) at 80; for 3 h;Catalytic behavior;
Steps:
5 2-(4-Nitro-but-2-enyl)-4,5-dihydro-1H-imidazole
General procedure: A mixture of nitrile (1.0 mmol), ethylenediamine (2.0 mmol) and catalyst (4 mol%) were heated under solvent-free conditions with stirring at 80°C. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL), and filtered. The filtrate was concentrated in vacuo, and the resulting residue was purified by column chromatography to provide the desired product. The products were characterized by elemental analyses, 1H NMR [49],31C NMR and ESI-MS spectra. 2.6.5 ;4-(4,5-dihydro-1H-imidazol-2-yl)-phenylamine; Anal. Calc. for C9H11N3 (161.20 g, mol-1): C, 67.06; H, 6.88; N, 26.07%. Found: C, 67.42; H, 6.54; N, 26.81%. 1H NMR (DMSO-d6, δ): 7.02-7.18 (d, 2H, aromatic CH), 6.88-6.92 (d, 2H, aromatic CH), 4.68 (s, 1H, NH), 4.36-4.49 (t, 2H, CH2), 4.10-4.21 (t, 2H, CH2), 3.82 (s, 2H, NH2). ;13C NMR (DMSO-d6, δ): 164.7, 149.2, 133.0, 128.5, 116.1, 54.8, 35.5. ESI-MS, m/z: 161.1 [M]+.
References:
Manikandan, Rajendran;Anitha, Panneerselvam;Prakash, Govindan;Vijayan, Paranthaman;Viswanathamurthi, Periasamy;Butcher, Ray Jay;Malecki, Jan Grzegorz [Journal of Molecular Catalysis A: Chemical,2015,vol. 398,p. 312 - 324]
