1,1'-Carbonyldiimidazole → HCID 18412364, compound

Participants

Reaction Steps

532 mg (3.0 mmol) of 4-cyanophenyloxyacetic acid and 486 mg (3.0 mmol) of 1,1′-carbonyldiimidazole were dissolved in 40 mL of tetrahydrofuran and refluxed for 15 minutes. Then 700 mg (2.24 mmol) of 3-amino-4-methylaminobenzenesulfonic acid-N-methyl-N-(1-methylpiperidin-4-yl)amide were added and boiling was continued for a further eight hours. Then the mixture was evaporated down and the resulting oily residue was refluxed in 30 mL of glacial acetic acid for one hour. The glacial acetic acid was distilled off, the residue was mixed with about 30 mL of water and made alkaline with concentrated ammonia, and the solution was extracted three times with about 20 mL of dichloromethane. The organic phases were dried and evaporated down. The resulting product was further reacted without any purification. Yield: 400 mg (39% of theory), C23H27N5O3S (453.6); Rf value: 0.37 (silica gel; dichloromethane/ethanol=4:1).

Provenance & Evidence