[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[CH3:9][CH2:10][O:11][C:12]([CH2:14][C:15]([C:17](OCC)=O)=O)=[O:13].P(Cl)(Cl)([Cl:24])=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[NH2:7][C:3]1[CH:2]=[C:1]2[C:6]([C:14]([C:12]([O:11][CH2:10][CH3:9])=[O:13])=[CH:15][C:17]([Cl:24])=[N:8]2)=[CH:5][CH:4]=1To 25 g (231 mmol) of m-phenylenediamine was added 43 g (231 mmol) of diethyl oxaloacetate, followed by stirring at 160 degrees for 1 hour. After standing to cool, the crystals were washed with methanol. To a solution of the crystals (3.0 g, 13 mmol) in chloroform (30 ml) was added phosphorus oxychloride (3.6 ml), followed by heating under reflux for 1 hour. After standing to cool, the reaction mixture was poured onto ice water, basified with 1 N sodium hydroxide aqueous solution, and the resulting crystals were collected by filtration. The crystals were washed with tetrahydrofuran and the filtrate was evaporated, to give 4.85 g of the title compound.
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