Sodium Azide → HCID 86678051, compound

Participants

Reaction Conditions

Reaction Steps

To 1 mL of DMF/H2O (v/v=9/1) was added 2-(2-(2-bromoethoxy)ethoxy)isoindoline-1,3-dione (50 mg, 0.17 mmol) and sodium azide (16.6 mg, 0.26 mmol). The mixture was heated to 80° C. overnight. Then it was allowed to cool down to room temperature and was extracted with ethyl acetate for 3 times. The combined organic layers were washed with brine and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure, the crude product was purified by silica gel column chromatography (hexanes: ethyl acetate 2:1) to afford 2-(2-(2-azidoethoxy)ethoxy)isoindoline-1,3-dione (44 mg, 0.17 mmol, 100%) as colorless oil. 1H NMR (CDCl3, 500 MHz) δ (ppm): 3.28 (t, J=4.7 Hz, 2H), 3.64 (t, J=4.8 Hz, 2H), 3.84 (t, J=3.8 Hz, 2H), 4.34 (t, J=3.9 Hz, 2H), 7.71 (dd, J=2.6, 4.7 Hz, 2H), 7.79 (dd, J=3.2, 5.0 Hz, 2H).

Provenance & Evidence