Cesium carbonate → 2-[2-(1H-1,2,3-Triazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione

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Reaction Conditions

Reaction Steps

Add 1H-1,2,3-triazole (250 g; 3.51 mol), N-(2-bromoethyl)phthalimide (942 g; 3.52 mol) and 1500 mL of DMF to a 5-L roundbottom flask fitted with a mechanical stirrer, nitrogen inlet and temperature probe. Cool the mixture to 15° C. Stir the mixture until all of the solids are nearly dissolved and then cool in an ice-water bath. Add cesium carbonate (1145 g; 3.51 mol) in portions over 10 min. The reaction mixture exotherms to 21° C. Allow the mixture to stir and come to RT overnight. Pour the reaction mixture into a 12-L flask containing 8 L of ice-water. Stir the suspension for 30 min and then filter and rinse the solid with 3 L of water. Air-dry for 2 h. Recrystallize the mixture of regioisomers from 7 L of absolute ethanol. Isolate the solid by filtration and air-dry. Recrystallize again from 16 L of absolute ethanol. Isolate the solids by filtration and rinse with fresh ethanol (1000 mL). Vacuum-dry the solids at 40° C. to give the title compound, 292.7 g (34%) as a white solid. MS (EI) m/z 243 [M+1]+.

Provenance & Evidence