[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7]([CH:11]=1)[C:8]([OH:10])=O)=[O:2].C(N(CC)CC)C.C(Cl)(=O)OCC.[F:27][C:28]([F:38])([F:37])[C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1>C(Cl)Cl>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7]([CH:11]=1)[C:8]([NH:34][CH2:33][C:32]1[CH:31]=[CH:30][C:29]([C:28]([F:27])([F:37])[F:38])=[CH:36][CH:35]=1)=[O:10])=[O:2]To a suspension of 1.00 g of 5-formyl-2-methoxybenzoic acid in 50 ml of methylene chloride were added 1.00 ml of triethylamine and 0.60 ml of ethyl chlorocarbonate, and the mixture was stirred for 15 minutes at room temperature. Then, a solution of 1.17 g of 4-trifluoromethylbenzylamine in 10 ml of methylene chloride was added and the mixture was stirred further for 3 hours at room temperature. After washed with water, the reaction mixture was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue obtained was purified by means of column chromatography (silica gel, hexane:ethyl acetate=1:1) and then recrystallized from a mixed solvent of diethyl ether-ethyl acetate-hexane to obtain 1.46 g of 5-formyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide as colorless crystals.
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