[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].CS(O[CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH3:19])(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:19][O:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:7][C:2]1[C:1]([NH2:8])=[CH:6][CH:5]=[CH:4][CH:3]=1To a solution of phenylenediamine (10.8 g) and 4-methoxybutyl methanesulfonate (9.11 g) in acetonitrile (100 ml) was added potassium carbonate (20.7 g), and the mixture was stirred heated under reflux for 15 hr. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (35:65) was concentrated under reduced pressure to give the object product (5.44 g).
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