Propargyl bromide → N-(Prop-2-ynyloxy)phthalimide

Participants

Reaction Steps

To a stirred solution of N-hydroxyphthalimide (50.5 g) and propargyl bromide (37.0 g) in DMF (250 ml) at 0° C. was added drop-wise triethylamine (50 ml). The cooling bath was removed and the reaction mixture was stirred at room temperature for 4 hours. The mixture was poured into water containing some ice and the precipitated material was isolated by filtration. The crude product was recrystallised from ethanol and gave 2-prop-2-ynyloxy-isoindole-1,3-dione (47.5 g). Step 2: The above obtained phthalimide intermediate (1 mmol) was mixed with p-tolyl isocyanate (2.8 mmol), triethylamine (0.05 mmol) and 1-nitrobutane (1.44 mmol) in toluene (3 ml). The reaction mixture was stirred at room temperature for 48 hours, filtrated and subjected to column chromatography on silica, affording 2-(3-propyl-isoxazol-5-ylmethoxy)-isoindole-1,3-dione. Step 3: The above cycloaddition product was dissolved in methanol+dichloromethane and hydrazine monohydrate (1 eq.) was added. The reaction mixture was stirred at room temperature for 20 hours and placed at 5° C. for 3 hours. The solid material was removed by filtration and the filtrate was evaporated under reduced pressure and gave the title compound. 13C-NMR (DMSO-d6) δ 169.0, 163.2, 103.0, 67.4, 27.2, 21.0, 13.5.

Provenance & Evidence