Reaction #452464

Reaction equation

N-(4-bromobenzyl)-N-(3-isothiocyanatopropyl)-N-(pyridin-2-yl)amine

3-(1-triphenylmethylimidazol-4-yl)propylamine

→

1-[3-(1-triphenylmethylimidazol-4-yl)propyl]-3-[3-[N-(4-bromobenzyl)-N-(pyridin-2-yl)amino]propyl]thiourea

Yield 80.0%

Solvents

chloroform

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureat reflux for 4 h
3. 3
   OtherThe solvent was removed by evaporation in vacuo
4. 4
   Otherthe residue (3.09 g) purified by column chromatography on silica gel (400 ml)

Procedure

N-(4-bromobenzyl)-N-(3-isothiocyanatopropyl)-N-(pyridin-2-yl)amine(1 g, 2.76 mmol) and 3-(1-triphenylmethylimidazol-4-yl)propylamine (1.014 g, 2.76 mmol) were dissolved in chloroform (10 ml) and heated at reflux for 4 h. The solvent was removed by evaporation in vacuo and the residue (3.09 g) purified by column chromatography on silica gel (400 ml) using ethyl acetate/methanol/triethylamine 9:0.5:0.5 as eluent affording 1.59 g (80%) of pure 1-[3-(1-triphenylmethylimidazol-4-yl)propyl]-3-[3-[N-(4-bromobenzyl)-N-(pyridin-2-yl)amino]propyl]thiourea.

Source