Reaction #452463

Reaction equation

N-(4-bromobenzyl)-N-(pyridin-2-yl)-propane-1,3-diamine

carbondisulfide

→

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

Yield 88.3%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   FiltrationThe reaction mixture was filtered
2. 2
   Otherthe solvent evaporated in vacuo
3. 3
   ExtractionThe residue (5.29 g) was extracted with diethyl ether (3×20 ml)
4. 4
   Otherthe combined organic extracts were evaporated in vacuo

Procedure

To a solution of N,N-dicyclohexylcarbodiimide (2.08 g, 10 mmol) in dry tetrahydrofuran (20 ml) was slowly added at -10° C. a solution of N-(4-bromobenzyl)-N-(pyridin-2-yl)-propane-1,3-diamine (3.20 g, 10 mmol) and carbondisulfide (4.3 ml, 70 mmol) in dry tetrahydrofuran (20 ml) under an atmosphere of nitrogen. The mixture was stirred at -10° C. for 3 h and for 48 h at room temperature. The reaction mixture was filtered and the solvent evaporated in vacuo. The residue (5.29 g) was extracted with diethyl ether (3×20 ml) and the combined organic extracts were evaporated in vacuo affording 3.2 g (88%) of N-(4-bromobenzyl)-N-(3-isothiocyanatopropyl)-N-(pyridin-2-yl)amine as an oil.

Source