Hydrochloric Acid → HCID 11684859, compound

Participants

Reaction Steps

Combine 4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-N-(4-cyano-phenyl)-benzenesulfonamide (1.44 g, 3.10 mmol), sodium azide (2.02 g, 31.0 mmol) and triethyl ammonium chloride (4.27 g, 31.0 mmol) in toluene (10.3 mL) and heat to reflux for 2 hours. Cool to ambient temperature and add 1N hydrochloric acid (20 mL) and ethyl acetate (20 mL). Extract the aqueous phase with ethyl acetate (2×20 mL), dry (sodium sulfate) and condense under reduced pressure. Sonicate resulting red residue in diethyl ether for 1 hour, collect the title compound by filtration as a white solid (831 mg, 1.64 mmol): 1H NMR (DMSO-d6) δ 0.82 (t, 3H), 1.45 (m, 2H), 2.57 (m, 5H), 5.30 (s, 2H), 6.62 (d, 1H), 7.30 (m, 1H), 7.45 (t, 1H), 7.60 (m, 2H), 7.67 (m, 2H), 7.78 (d, 1H), 7.85 (m, 3H), 10.65 (s, 1H), 12.82 (s, 1H) tetrazole H not observed; MS (m/z): 506 (M−1). The following compounds are prepared essentially by the method of Example 8.

Provenance & Evidence