thiourea in water T=100°C; 12 h; Heating;

1: NaBH4 / aq. ethanol 2: I2; PPh3; imidazole 4: TFA View Scheme

1: I2; PPh3; imidazole 3: TFA View Scheme

1: 90 percent / LiBH4, cc. HCl / bis-(2-methoxy-ethyl) ether / 3 h 2: 48percent HBr, cc. sulfuric acid / 6 h / Heating 3: thiourea / H2O / 12 h / 100 °C / Heating View Scheme

1: 84 percent / pyridine / 3 h 2: 90 percent / LiBH4, cc. HCl / bis-(2-methoxy-ethyl) ether / 3 h 3: 48percent HBr, cc. sulfuric acid / 6 h / Heating 4: thiourea / H2O / 12 h / 100 °C / Heating View Scheme

1: 85 percent / thionyl chloride / dimethylformamide / 4 h / Heating 2: 84 percent / pyridine / 3 h 3: 90 percent / LiBH4, cc. HCl / bis-(2-methoxy-ethyl) ether / 3 h 4: 48percent HBr, cc. sulfuric acid / 6 h / Heating 5: thiourea / H2O / 12 h / 100 °C / Heating View Scheme

2: TFA View Scheme