1: 1.) Na 2: LiAlH4 / diethyl ether / 18 h / 35 °C 3: 48percent HBr, conc. H2SO4 / 18 h / 95 - 100 °C 4: 1.) thiourea; 2.) tetraethylenepentamine / 1.) ethylene glycol, 75 deg C, 18 h; 2.) 75 deg C, 2 h View Scheme

1: LiAlH4 / diethyl ether / 18 h / 35 °C 2: 48percent HBr, conc. H2SO4 / 18 h / 95 - 100 °C 3: 1.) thiourea; 2.) tetraethylenepentamine / 1.) ethylene glycol, 75 deg C, 18 h; 2.) 75 deg C, 2 h View Scheme

Tetraethylenepentamine; thiourea 1.) ethylene glycol, 75 deg C, 18 h; 2.) 75 deg C, 2 h; Yield given. Multistep reaction;

1: 48percent HBr, conc. H2SO4 / 18 h / 95 - 100 °C 2: 1.) thiourea; 2.) tetraethylenepentamine / 1.) ethylene glycol, 75 deg C, 18 h; 2.) 75 deg C, 2 h View Scheme