Semicarbazide hydrochloride → 2-(4-{(3E)-4-{2-[(4-tert-Butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}-benzoyl)hydrazinecarboxamide

Participants

Reaction Steps

836 mg (6.62 mmol) of oxalyl chloride are slowly added dropwise to a solution of 600 mg (1.10 mmol) of 4-{(3E)-4-{2-[(4-tert-butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoic acid from Example 105A in 6 ml of dry toluene with 4 drops of DMF while cooling in ice. The reaction mixture is stirred at RT for 10 minutes and then heated to reflux for 1 hour. After cooling, the mixture is concentrated in vacuo, and the residue is coevaporated twice with toluene and then taken up in 6 ml of THF. This solution is added dropwise to a previously prepared solution of 135.4 mg (1.21 mmol) of semicarbazide hydrochloride and 88.3 mg (2.21 mmol) of sodium hydroxide in 1 ml of THF and 0.25 ml of water at 0° C. The mixture is stirred at 0° C. for 2 hours and then at RT for 30 minutes, and the residue after concentration is reacted without further purification in the next stage.

Provenance & Evidence