hydrogenchloride; potassium hydroxide in ethanol; water 1 h; Heating;

1: SOCl2 / DMF / 0.67 h / Heating 2: 93 percent / triethylamine / CHCl3 / 1.) -5 to 0 deg C, 30 min; 2.) r.t., 1 h 3: PCl5 / benzene / 0.25 h / 75 °C 4: sodium azide / dimethylformamide / 0.5 h 5: 1.) 3M KOH, 2.) 15percent HCl / methanol; H2O / 1 h / Heating View Scheme

1: 93 percent / triethylamine / CHCl3 / 1.) -5 to 0 deg C, 30 min; 2.) r.t., 1 h 2: PCl5 / benzene / 0.25 h / 75 °C 3: sodium azide / dimethylformamide / 0.5 h 4: 1.) 3M KOH, 2.) 15percent HCl / methanol; H2O / 1 h / Heating View Scheme

1: PCl5 / benzene / 0.25 h / 75 °C 2: sodium azide / dimethylformamide / 0.5 h 3: 1.) 3M KOH, 2.) 15percent HCl / methanol; H2O / 1 h / Heating View Scheme

1: sodium azide / dimethylformamide / 0.5 h 2: 1.) 3M KOH, 2.) 15percent HCl / methanol; H2O / 1 h / Heating View Scheme

1: 50 percent / EtONa / ethanol / 16 h / Heating 2: 94 percent / 1.) KOH; 2.) 15percent HCl / ethanol; H2O / 1 h / Heating View Scheme