[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1.Cl[C:20](=[O:25])[C:21]([O:23][CH3:24])=[O:22].CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:24][O:23][C:21](=[O:22])[C:20]([N:12]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[C:8](=[O:11])[CH2:9][CH3:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:25]To a solution of 1-(4-chloro-2-phenylamino-phenyl)-propan-1-one (13.0 g, 50.2 mmol) in toluene (150 mL) was added methyl chlorooxoacetate (42.86 g, 350.0 mmol) at room temperature under nitrogen. The reaction mixture was heated at reflux at 110° C. for 16 hr. Completion of the reaction was monitored by silica TLC (mobile phase; hexane:ethyl acetate=1:1; Rf=0.5). The reaction mixture was concentrated under vacuum to afford 15.2 g (87.6% crude yield) of N-(5-chloro-2-propionyl-phenyl)-N-phenyl-oxalamic acid methyl ester. The crude product was used in the next step without further purification.
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