[Cl:1][C:2]1[C:11]([C:12]([NH:14][O:15][CH3:16])=[O:13])=[C:10]([Cl:17])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:18](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CN(C)C=O>[Cl:1][C:2]1[C:11]([C:12](=[N:14][O:15][CH3:16])[O:13][CH3:18])=[C:10]([Cl:17])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]A mixture of 16.0 g (0.058 mol) of methyl 2,4-dichloro-3-methoxyaminocarbonylbenzoate and 10.1 g (0.073 mol) of potassium carbonate in 300 ml of dimethylformamide was stirred at room temperature for 30 minutes. 11.0 g (0.087 mol) of dimethyl sulfate were then added, the mixture was stirred for 12 hours at room temperature, and a further 11.0 g of dimethyl sulfate were added. The reaction mixture was heated to 60° C. for 6 hours, cooled and stirred into 2 l of ice-water. The aqueous phase was then extracted with ethyl acetate, the combined organic phases were dried and the solvent was distilled off under reduced pressure. Silica gel chromatography of the residue (eluent:toluene/ethyl acetate=9/1) afforded 2.0 g of methyl 2,4-dichloro-3-(1′-methoxyimino-1-(methoxy)methyl)benzoate.
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