N,N'-Dimethylethylenediamine → 2-(2-methoxyphenyl)-1,3-dimethylimidazolidine

Reaction equation

[CH:1](=O)[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH3:11][NH:12][CH2:13][CH2:14][NH:15][CH3:16].[O-]S([O-])(=O)=O.[Mg+2]>C(O)C>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:1]1[N:15]([CH3:16])[CH2:14][CH2:13][N:12]1[CH3:11]

Participants

Procedure

A solution of o-anisaldehyde (9.0 g, 66 mmol) and N,N′-dimethylethylenediamine (7.9 mL, 73 mmol) in ethanol (180 mL) was stirred at r.t. for overnight. MgSO4 (30 g) was added and the mixture was stirred for 20 min. The reaction mixture was filtered and washed with ether. The solvent was removed in vacuo to afford 2-(2-methoxyphenyl)-1,3-dimethylimidazolidine as a light yellow solid, 12 g, yield 88%. 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 2.21 (s, 6H) 2.57-2.72 (m, 2H) 3.34 (d, J=2.75 Hz, 2H) 3.82 (s, 3H) 4.13 (s, 1H) 6.88 (d, J=8.24 Hz, 1H) 7.00 (t, J=7.48 Hz, 1H) 7.25-7.30 (m, 1H) 7.67 (d, J=7.63 Hz, 1H).