[C:1]([NH:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([Cl:18])=[CH:11][C:10]=1[C:19]([F:22])([F:21])[F:20])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2].[CH3:23]I.[H-].[Na+]>CN(C)C=O>[C:1]([N:8]([CH3:23])[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([Cl:18])=[CH:11][C:10]=1[C:19]([F:20])([F:21])[F:22])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2]To a stirred solution of N-ethoxalyl-4-chloro-6-nitro-2-trifluoromethylaniline (11 g. 32.3 mmol) and methyl iodide (3.0 ml, 48 mmol) in dry dimethylformamide (DMF, 50 ml) was added in portions sodium hydride (total 1.7 g, 39 mmol). External cooling was used to keep the reaction temperature below 25° C. Stirring was continued at room temperature for 3 h, whereafter the solvent was removed by evaporation in vacuo. The residue was then partitioned between ether and water. The organic phase was washed twice with water, dried over Na2SO4 and evaporated. This treatment left the title compound as an oil, which was processed without further purification.
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