[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[Na+].[I-].C([O-])([O-])=O.[K+].[K+].[CH2:19]([O:22][CH2:23][CH2:24]Cl)[CH2:20]Cl>CN(C=O)C.O>[O:22]1[CH2:23][CH2:24][N:1]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=2)[CH2:20][CH2:19]1To a solution of 4-aminobenzamide (6.81 g, 50 mmol) in DMF (70 mL) were added NaI (22.48 g, 150 mmol) and K2CO3 (13.82 g, 100 mmol). The mixture was heated to 140° C. and 2,2′-dichlorodiethyl ether (14.30 g, 100 mmol) was added. The reaction mixture was heated at 150° C. for 5 h, and cooled to rt. The mixture was diluted with water (100 mL), stirred for 10 min, and filtered. The filter cake was washed with water and dried to give the title compound as a yellow solid (6.60 g, 64%).
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