4-toluenesulfonyl azide; sodium hydride in tetrahydrofuran 48 h; Ambient temperature;

1: SOCl2 / 3 h / Heating 2: NaN3 / H2O / 0.5 h / Ambient temperature 3: benzene / 6 h / Heating 4: conc. hydrochloric acid / acetone / 0.5 h 5: 92 percent / NaH, p-tosyl azide / tetrahydrofuran / 48 h / Ambient temperature View Scheme

1: NaN3 / H2O / 0.5 h / Ambient temperature 2: benzene / 6 h / Heating 3: conc. hydrochloric acid / acetone / 0.5 h 4: 92 percent / NaH, p-tosyl azide / tetrahydrofuran / 48 h / Ambient temperature View Scheme

1: 78 percent / conc. hydrochloric acid / methanol / 24 h / 110 °C 2: 92 percent / NaH, p-tosyl azide / tetrahydrofuran / 48 h / Ambient temperature View Scheme

1: conc. hydrochloric acid / acetone / 0.5 h 2: 92 percent / NaH, p-tosyl azide / tetrahydrofuran / 48 h / Ambient temperature View Scheme

in gaseous matrix T=-261.2°C; Irradiation;