Azidotrimethylsilane → HCID 59327682, compound

Participants

Reaction Conditions

Reaction Steps

Following the procedure of Moses and coworkers (K. Barral, A. D. Moorhouse, J. E. Moses, Org. Lett. 2007, 9, 1809-1811). N-(4-aminophenyl)-4-methylbenzene-1-sulfonamide (1.00 g, 3.81 mmol) was dissolved in anhydrous CH3CN (6 mL), and the resulting solution was placed under Ar(g) and cooled to 0° C. To this was added t-BuONO (0.68 mL, 5.71 mmol) followed by TMSN3 (0.60 mL, 4.57 mmol) dropwise. The resulting solution was allowed to warm to room temperature and stirred for 2 h. The resulting mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, eluting with 10% EtOAc/hexanes, to give aryl azide 7 (1.02 g, 3.54 mmol, 93% yield) as a white solid.

Provenance & Evidence