C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[OH:18].C([N:21](CC)[C:22](=[O:33])[C:23]1[CH:28]=[C:27](F)[CH:26]=[CH:25][C:24]=1[N+:30]([O-:32])=[O:31])C.O>CS(C)=O.C1C=CC=CC=1.CCCCCC>[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([F:16])([F:17])[F:15])[CH:11]=[CH:10][C:9]=1[O:18][C:27]1[CH:26]=[CH:25][C:24]([N+:30]([O-:32])=[O:31])=[C:23]([CH:28]=1)[C:22]([NH2:21])=[O:33]To a 100 ml flask fitted with a magnetic stirrer and drying tube is added dimethyl sulfoxide (30 ml), anhydrous potassium carbonate (7.55 g, 0.054 mole) and 2-chloro-4-trifluoromethylphenol (10.3 g, 0.052 mole). The mixture is stirred at room temperature overnight. A solution of N,N-diethyl-5-fluoro-2-nitrobenzamide (12.5 g, 0.052 mole) in dimethyl sulfoxide (20 ml) is then added rapidly and the reaction mixture is stirred at room temperature for 60 hours. The reaction mixture is poured into water (500 ml) and the product extracted into carbon tetrachloride (4×100 ml), the combined extracts are dried over anhydrous magnesium sulfate and the solvent removed under vacuum to afford 15.3 g of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzamide (75% yield) Recrystallization from benzene/hexane affords substantially pure product mp. 75°-79° C. Elemental anal, Calcd. for C18H16ClF3N2O4 : C, 51.80; H, 3.88; Cl, 8.55; F, 13.68; N, 6.73. Found: C, 52.03; H, 3.90; Cl, 8.54; F, 13.59; N, 6.83.
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