Hydrochloric Acid → 1H-Imidazole-1-sulfonyl azide hydrochloride

Participants

Reaction Steps

A modification of a published procedure was used (19). A suspension of 6.53 g NaN3 (25, 100 mmol, Aldrich, >99.5%) and 100 mL acetonitrile (Aldrich, 99.8% anhydrous) in a 500-mL round-bottom flask was cooled in an ice water bath under a flow of nitrogen. Then was added 8.15 mL sulfuryl chloride (100 mmol, TCI American, >98.0%) in 20 mL) anhydrous acetonitrile drop-wise to the ice-cooled suspension. The mixture was stirred overnight at room temperature, after which we cooled the white suspension to −0° C. with ice water and added 13.03 g imidazole (191 mmol, TCI America, >98.0%). The resulting white slurry was warmed to room temperature, then stirred for 3 h. It was diluted with ethyl acetate (200 mL) and separated and discarded the aqueous layer. The organic layer was washed twice with deionized water (2×100 mL), then twice with saturated aqueous NaHCO3 (2×100 mL). It was dried over anhydrous MgSO4 overnight and filtered. Ethanolic HCl solution (196 mmol) was added drop-wise to the filtrate while stirring at ice-water temperature. After the addition of −3 mL, a large amount of white solid appeared. The mixture was kept in an ice bath for 15 min, then at room temperature for 30 min, after which it was filtered. The filter cake was washed with ethyl acetate (3×100 mL) to obtain 126 as a colorless solid (8.65 g, 49.9%), m.p. 99-101° C. IR (KBr) 2173, 1383 and 1160 cm−1. 1H NMR (500 MHz, D2O) δ 7.61 (dd), 8.02 (dd), 9.39 (dd); 13C NMR (125. MHz, D2O) δ=120.0, 123.5, 137.6. Element Analysis Calculated C, 17.19; H, 1.92; N, 33.41. Found: C, 17.38; H, 1.98; N, 32.97.

Provenance & Evidence