Triethylamine → HCID 86718989, compound

Participants

Reaction Steps

To 4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)aniline (I-7b: 1.339 g, 5.69 mmol) in THF (37.9 mL) at 0° C. was added 4-nitrophenyl chloroformate (2.064 g, 10.24 mmol) and triethylamine (1.420 mL, 10.24 mmol). The mixture was stirred at room temperature for 1 hour. Then ethyl carbazate (1.540 g, 14.79 mmol) and more triethylamine (1.420 mL, 10.24 mmol) were added. The mixture was stirred at room temperature for 16 hours, followed by the addition of aqueous saturated sodium bicarbonate. The mixture was then extracted twice with ethyl acetate, dried over MgSO4, filtered, and then concentrated in vacuo. The crude product was purified by silica gel chromatography (40-100% ethyl acetate/heptane) giving ethyl 2-(4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)phenylcarbamoyl)-hydrazinecarboxylate (I-7c: 1.31 g, 63%) as a foamy colorless oil. LC-MS (M+1) 366.1, t=0.95 minute.

Provenance & Evidence