1: thionyl chloride / 1,2-dichloro-ethane / 4 h / Reflux 2: ammonia / 1,2-dichloro-ethane / 20 °C 3: palladium 10 on activated carbon; hydrogen / methanol 4: sodium hydrogensulfite / N,N-dimethyl acetamide / 3 h / 150 °C 5: thionyl chloride / 1,2-dichloro-ethane; N,N-dimethyl-formamide / 0.5 h / 50 °C 6: N,N-dimethyl-formamide / 2 h / 50 °C View Scheme

1: palladium 10 on activated carbon; hydrogen / methanol 2: sodium hydrogensulfite / N,N-dimethyl acetamide / 3 h / 150 °C 3: thionyl chloride / 1,2-dichloro-ethane; N,N-dimethyl-formamide / 0.5 h / 50 °C 4: N,N-dimethyl-formamide / 2 h / 50 °C View Scheme

1: ammonia / 1,2-dichloro-ethane / 20 °C 2: palladium 10 on activated carbon; hydrogen / methanol 3: sodium hydrogensulfite / N,N-dimethyl acetamide / 3 h / 150 °C 4: thionyl chloride / 1,2-dichloro-ethane; N,N-dimethyl-formamide / 0.5 h / 50 °C 5: N,N-dimethyl-formamide / 2 h / 50 °C View Scheme

1.1: oxygen / dimethyl sulfoxide / 12 h / 100 °C 2.1: oxygen; trichlorophosphate / dimethyl sulfoxide; N,N-dimethyl-formamide / 50 °C 2.2: 50 °C View Scheme

1.1: oxygen / dimethyl sulfoxide / 12 h / 100 °C 2.1: oxygen; trichlorophosphate / dimethyl sulfoxide; N,N-dimethyl-formamide / 50 °C 2.2: 50 °C View Scheme