[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.[I:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:21])=[C:18]([CH:20]=1)[NH2:19].Cl>C(N(CC)CC)C>[I:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:21])=[C:18]([NH:19][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:20]=12.1 mL of benzoyl chloride was added to 70 mL of a methylene chloride solution containing 3.5 g of 5-iodo-2-methylaniline and 2.5 mL of triethylamine at room temperature and stirred at the same temperature for 30 minutes. 1.0 mol/L hydrochloric acid was added to the reaction mixture. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution, and the solvent was evaporated under reduced pressure. Diisopropyl ether and hexane were added to the obtained residue and a solid substance was separated by filtration to obtain 4.2 g of N-(5-iodo-2-methylphenyl)benzamide as pale yellow solid.
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