sodium azide; sulfuric acid; urea; sodium nitrite in water; acetic acid T=0°C; 1 h; in the dark;

1: 86 percent / 2 N KOH / methanol / 3 h / Heating 2: 74 percent / concd. H2SO4, NaNO2, urea, NaN3 / acetic acid; H2O / 1 h / 0 °C / in the dark View Scheme

1: 27 percent / 1 h / 100 °C 2: 86 percent / 2 N KOH / methanol / 3 h / Heating 3: 74 percent / concd. H2SO4, NaNO2, urea, NaN3 / acetic acid; H2O / 1 h / 0 °C / in the dark View Scheme