P-Toluenesulfonylhydrazide → HCID 18428684, compound

Participants

Reaction Steps

The vinylsulfonamide from example 67 (1.26 g, 3.33 mmol) was heated together with tosyl hydrazine (6.20 g, 33.3 mmol) in toluene at reflux for 5 h. After cooling to rt the solvent was evaporated and the residue partitioned between EtOAc (50 mL) and sat. NaHCO3 (50 mL). The organic layer was separated, washed with water (20 mL), brine (20 mL) and then dried (MgSO4) and evaporated. The residue was purified by flash chromatography [SiO2; (EtOAc/ MeOH/ 880 NH3; 100:5:0.5)/ pentane; 3:1→1:0] to afford the desired product as a cream powder (1.055 g, 83%); Free base: δH(CD3OD, 400 MHz) 2.27 (6 H, s), 2.47 (3 H, s), 3.09-3.13 (2 H, m), 3.30-3.36 (2 H, m), 3.50 (2 H, m), 6.83 (1 H, d), 6.87 (2 H, d), 7.19 (1 H, d), 7.27 (2 H, d), 7.35 (1 H, s); MS m/z (TS+) 381 (MH+).

Provenance & Evidence