[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C([N:19]1[CH:23]=[CH:22]N=C1)(N1C=CN=C1)=O.[CH3:24][C:25]1[CH:26]=[C:27](CCN)[CH:28]=[CH:29][CH:30]=1>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:19][CH2:23][CH2:22][C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:24])=[O:9])=[CH:10][CH:11]=1A solution of 4-methoxybenzoic acid (5.7 g, 0,038 mol) and carbonyldiimidazole (6.1 g, 0.050 mol) in 100 ml of THF was stirred for 1 h protected from moisture. To this was added 2-(3-methylphenyl) ethylamine and stirring was continued overnight. The reaction mixture was diluted with water (500 ml) and extracted with two 150 ml portions of methylene chloride. The methylene chloride solution was washed with 250 ml of water and evaporated to give the crystalline amide which was recrystallized from CH3OH/water to give 6.8 g (67%) H1, mp 87-92°.
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