[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH3:19])[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])(=[O:3])[CH3:2].[H-].[Na+].[CH3:22]I.O>CN(C)C=O>[CH3:22][CH2:2][C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH3:19])[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])=[O:3]To a solution of 40.0 g of 2-acetylamino-3-(o-chlorobenzoyl)-4-methylthiophene in 800 ml of dimethylformamide is added 7.74 g of 63 % sodium hydride. The mixture is stirred at room temperature for 30 minutes. Then 61.34 g of methyl iodide in 184 ml of dimethylformamide is added thereto. The mixture is stirred at room temperature for 2 hours, then poured into water, and extracted with benzene. The benzene extracts are washed with water, dried over sodium sulfate, and the solvent is removed under reduced pressure. The residual oil is chromatographed on silica gel, using chloroform as an eluent to give 2-(N-methylacetylamino)-3-(o-chlorobenzoyl)-4-methylthiophene as an oil.
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