[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH3:10]CN(C(C)C)C(C)C.C(Cl)(Cl)=S.[Cl:23][C:24]1[C:29]([Cl:30])=[CH:28][C:27]([NH2:31])=[C:26]([NH2:32])[CH:25]=1.CI.C(Cl)Cl.[Cl-].[Na+].O>C(Cl)Cl.CO>[Cl:23][C:24]1[C:29]([Cl:30])=[CH:28][C:27]2[NH:31][C:10]([NH:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[N:32][C:26]=2[CH:25]=1To a solution of 4-anisidine (6.5 mmol, 800 mg) and DIEA (7.2 mmol, 1.24 mL) in CH2Cl2 (10 mL) cooled to 0° C. was added thiophosgene (6.5 mmol, 500 μL) dropwise. The solution was allowed to reach ambient temperature for 1 h, and 4,5-dichloro-1,2-phenylenediamine (6.5 mmol, 1.15 g) was added to the reaction. The reaction mixture was heated at 40° C. for 16 h, and MeI (7.2 mmol, 445 μL) and DIEA (7.2 mmol, 1.24 μL) were added. The reaction was heated at 40° C. for 8 h, and allowed to stand at ambient temperature for 16 h. Aqueous workup with CH2Cl2/brine, followed by flash chromatography on silica eluting with 4% MeOH in CH2Cl2 afforded the product as a brown oil. LC-MS (ESI, Method B): 1.62 min, m/z 308.2 (M+1).
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