Sodium hydride → HCID 22327360, compound

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[N:13]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26])[C:14](=[O:18])OCC.[H-].[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:8][C:6]1[CH:5]=[C:4]([C:9]([F:10])([F:11])[F:12])[C:3]2[N:13]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[C:14](=[O:18])[NH:1][C:2]=2[CH:7]=1

Participants

Procedure

Ethyl 2,4-diamino-6-(trifluoromethyl)phenyl(2,4-dichlorophenyl)carbamate (1.1454 g) was dissolved in ethanol (20 ml), and to the solution was added sodium hydride (112.2 mg). The reaction mixture was heated at reflux for 6 hours. After allowing to cool, to the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by silica gel column (60 g, CHCl3:methanol=10:1→5:1) to give the title compound (0.8058 g, 79%).