N-(4-chlorophenyl)benzene-1,2-diamine → HCID 70979050, compound

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Reaction Steps

To a stirred refluxing solution of N1-(4-chlorophenyl)benzene-1,2-diamine (200 mg, 0.92 mmol) in toluene (20 mL) was added drop-wise a solution of 2,2-dimethylmalonyl dichloride (155 mg, 0.92 mmol). Then the mixture was refluxed for 1 h. The solvent was removed in vacuum, stirred with water (20 mL), extracted with DCM (20 mL×3). The combined organic layer was dried over Na2SO4. The mixture was concentrated in vacuum and the residue was purified by column chromatography (silica-gel, DCM: methanol=40:1) to give 1-(4-chlorophenyl)-3,3-dimethyl-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione as a yellow solid (167.5 mg, 58%). LRMS (M+H+) m/z: calcd 314.08. found 314.

Provenance & Evidence