pyridine; thionyl chloride in benzene 3 h; Heating;

1: 25 percent / tosyl azide / ethanol / 0.5 h / 15 - 20 °C 2: 93 percent / 2N aq. NaOH / ethanol / 1 h / 50 °C 3: 100 percent / SOCl2, pyridine / benzene / 3 h / Heating View Scheme

1: 1.) Na, 2.) tosyl azide / 1.) EtOH, 15-20 deg C, 2.) EtOH, 0.5 h 2: 93 percent / 2N aq. NaOH / ethanol / 1 h / 50 °C 3: 100 percent / SOCl2, pyridine / benzene / 3 h / Heating View Scheme

1: 93 percent / 2N aq. NaOH / ethanol / 1 h / 50 °C 2: 100 percent / SOCl2, pyridine / benzene / 3 h / Heating View Scheme