[Cl:1][C:2]([Cl:8])([Cl:7])[C:3](=[NH:6])OC.[N+:9]([C:12]1[CH:13]=[C:14](N)[C:15]([NH2:18])=[CH:16][CH:17]=1)([O-:11])=[O:10].O.C(OCC)(=O)C>C(O)(=O)C>[N+:9]([C:12]1[CH:17]=[CH:16][C:15]2[N:18]=[C:3]([C:2]([Cl:8])([Cl:7])[Cl:1])[NH:6][C:14]=2[CH:13]=1)([O-:11])=[O:10]At 0° C., 6.3 g (35.9 mmol, 1.1 eq.) of methyl 2,2,2-trichloroethaneimidoate were added dropwise to a solution of 5.0 g (32.7 mmol) of 4-nitrobenzene-1,2-diamine in 150 ml of glacial acetic acid. The reaction mixture was stirred at RT for 3 h and then added to 400 ml of water, and 300 ml of ethyl acetate were added. After phase separation, the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed twice with in each case 130 ml of saturated aqueous sodium bicarbonate solution and once with saturated aqueous sodium chloride solution, dried (sodium sulphate), filtered and concentrated under reduced pressure and dried. The crude product was triturated with pentane and left to stand overnight. The solid was then filtered off, washed with pentane and dried under reduced pressure. Yield: 10.1 g (purity 77%, 85% of theory)
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