hydrogenchloride; sodium azide; sodium nitrite in methanol T=-10°C;

1: 1.) sodium nitrite, HCl; 2.) sodium azide / 1.) water, 0 - 5 deg C, 10 min; 2.) water, 0 - 5 deg C 2: tosyl chloride, triethylamine / diethyl ether / Ambient temperature View Scheme

triethylamine; p-toluenesulfonyl chloride in diethyl ether Ambient temperature; Yield given;

hydrogenchloride; sodium azide; sodium nitrite 1.) water, 0 - 5 deg C, 10 min; 2.) water, 0 - 5 deg C; Yield given. Multistep reaction. Yields of byproduct given;