thionyl chloride; N,N-dimethyl-formamide in benzene 4 h; Heating;

1: 77 percent / sodium sulfite / H2O / 18 h / Heating 2: 67 percent / SOCl2, dimethylformamide / benzene / 4 h / Heating View Scheme

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; triphenylphosphine; tetrabutylammomium bromide / dichloromethane / 12 h / 20 °C 2: tetra-(n-butyl)ammonium iodide; sodium sulfite / ethanol; water / |Reflux 3: thionyl chloride / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

sodium azide in water; acetone