P-Phenylenediamine → HCID 86663467, compound

Participants

Reaction Steps

The compound (163 mg, 0.206 mmol) obtained in Example 63e and benzene-1,4-diamine (111 mg, 1.03 mmol) were suspended in a mixed solvent of dichloromethane (8 mL) and acetonitrile (8 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (59.0 mg, 0.309 mmol) and triethylamine (0.057 mL, 0.41 mmol) were added, and the mixture was stirred at room temperature for 3 hours. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (59.0 mg, 0.309 mmol) and 4-N,N-dimethylaminopyridine (0.5 mg, 0.004 mmol) were further added, and the mixture was stirred at room temperature for 13 hours. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and dichloromethane was added (×2) to separate the layers. The resulting organic layer was dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1→0:1, v/v) to give the title compound (141 mg; yield, 78%) as a light pink solid.

Provenance & Evidence