thionyl chloride Chlorination; Heating;

thionyl chloride; N,N-dimethyl-formamide Inert atmosphereReflux;

1: 70 percent / H2O / 160 °C 2: 100 percent / SOCl / Heating View Scheme

1: DIPEA 2: SOCl2 View Scheme

triethylamine in tetrahydrofuran T=20°C;

1.1: triethylamine / tetrahydrofuran; dichloromethane / 2 h / 40 °C 2.1: palladium on activated charcoal; hydrogen / water; ethanol / 50 °C / |Autoclave 3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.67 h / |Inert atmosphere; |Reflux 3.2: 7 h / |Inert atmosphere; |Reflux 3.3: 3 h / |Reflux 4.1: hydrogenchloride / ethanol; dichloromethane / 6 h / 15 - 30 °C 4.2: 15 - 30 °C 5.1: triethylamine / water; acetonitrile / 15 °C 6.1: acetone / |Heating View Scheme

1: Et3N / tetrahydrofuran / 20 °C 2: 65 percent / H2 / 10percent Pd/C / methanol / 20 °C View Scheme

1.1: Et3N / tetrahydrofuran / 20 °C 2.1: 65 percent / H2 / 10percent Pd/C / methanol / 20 °C 3.1: CDI / tetrahydrofuran / 50 °C 3.2: tetrahydrofuran / 24 h / Heating 4.1: glacial acetic acid / 1 h / Heating View Scheme

1: NH3 2: H2 / Pd/C / ethanol View Scheme

ammonia