[H-].[Na+].[C:3]([C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[NH:18][CH:19]=[O:20])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].[CH3:23]I>CN(C)C=O.O>[CH3:23][N:18]([C:12]1[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=1[C:3](=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH:19]=[O:20]Sodium hydride (0.8 mole, 38.4 g of 50% in mineral oil) was added to a solution of 197.4 g (0.76 mole) of N-(2-benzoyl-4-chlorophenyl)formamide in 800 ml dimethylformamide. When the evolution of hydrogen ceased, 184 g of methyl iodide was added dropwise at such a rate that the temperature of the reaction mixture slowly rose to 70°. The reaction mixture was stirred for 90 min., and then poured into 2 l. of water. The aqueous mixture was extracted four times with 300 ml portions of methylene chloride, and the combined extracts were washed with water, dried (MgSO4) and evaporated to dryness under reduced pressure. The residue was recrystallized from methanol to give 145.4 g (70% yield) of the N-methylformamide as colorless crystals: mp 93.5°-94.5°; 1H nmr (CDCl3) showed two methyl peaks at δ 2.94 and 3.23 ppm (ratio 70:30).
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