Ethylenediamine → (2'-methoxy-3'-nitro-biphenyl-4-yl]-4,5-dihydro-1H-imidazole

反応式

[N+:1]([C:4]1[C:5]([O:18][CH3:19])=[C:6]([C:10]2[CH:15]=[CH:14][C:13](C=O)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:20][CH2:21][CH2:22][NH2:23].BrN1C(=O)CC[C:26]1=O>ClCCl>[CH3:19][O:18][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][C:6]=1[C:10]1[CH:11]=[CH:12][C:13]([N:20]2[CH2:21][CH2:22][N:23]=[CH:26]2)=[CH:14][CH:15]=1

参加物

実験手順

To a solution of 3′-nitro-2′-methoxy-biphenyl-4-carbaldehyde 32a (4.0 g, 15.5 mmol) in 40 mL of dichloromethane under stirring, upon cooling by an ice-water bath, was added 1,2-diaminoethane (981 mg, 16.3 mmol). After the mixture was stirred for another 0.5 hours, 1-bromo-pyrrolidine-2,5-dione (2.91 g, 16.33 mmol) was added. Upon completion of the addition, the ice-water bath was removed. The reaction mixture was stirred overnight at room temperature. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound 2-[(2′-methoxy-3′-nitro-biphenyl-4-yl]-4,5-dihydro-1H-imidazole 32b (4.0 g, 86.9%) as yellow solid.