Dichloromethane → 5-(2-Acetamidomethyl-propan-2-yl)-2-(4-methylphenyl)benzimidazole

反応式

[C:1]([NH:4][CH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([NH2:16])[CH:10]=1)([CH3:8])[CH3:7])(=[O:3])[CH3:2].ClCCl.[CH3:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=O)=[CH:23][CH:22]=1>C(N(CC)CC)C>[C:1]([NH:4][CH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]2[N:15]=[C:20]([C:21]3[CH:29]=[CH:28][C:24]([CH3:25])=[CH:23][CH:22]=3)[NH:16][C:11]=2[CH:10]=1)([CH3:8])[CH3:7])(=[O:3])[CH3:2]

参加物

実験手順

To 4.4 g. of the 4-(2-acetamidomethylpropan-2-yl)-1,2-diaminobenzene (prepared in Example 1f) in 120 ml. dry dichloromethane are added 3.3 ml. triethylamine and then, with ice cooling, 3.06 g. 4-methylbenzoic acid chloride. After stirring the reaction mixture for 3 hours at ambient temperature, the solvent is removed in a vacuum. The residue is dissolved in water and extracted three times with dichloromethane, the organic phase is dried over anhydrous sodium sulphate, filtered and the solvent is removed in a vacuum. The residue (6.7 g.) is dissolved in glacial acetic acid and stirred for 3 hours at 70° C. The solvent is removed in a vacuum and the residue is purified by column chromatography (silica gel; dichloromethane containing 5% methanol). There is obtained 1.55 g. of the title compound; m.p. 230°-232° C.