Reaction #630366

Reaction equation

Triethylamine

chloropropylamine hydrochloride

n-hexyl isocyanate

→

1-(3-chloropropyl)-3-n-hexylurea

Yield 86.1%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Otherthe solvent was removed in vacuo
2. 2
   workup.ADDITIONThe residue was treated with ether
3. 3
   Filtrationthe colorless solid was filtered off
4. 4
   WashThe ether solution was then washed with water
5. 5
   Dryingdried (magnesium sulfate)
6. 6
   Concentrationconcentrated

Procedure

Triethylamine (35 g; 35 mmole) was slowly added to a mixture of chloropropylamine hydrochloride (39 g; 0.3 mol), n-hexyl isocyanate (38.2 g; 0.3 mole) and methylene chloride (500 ml). The resulting solution was stirred for one hour, and then the solvent was removed in vacuo. The residue was treated with ether, and the colorless solid was filtered off. The ether solution was then washed with water, dried (magnesium sulfate) and concentrated to give pure 1-(3-chloropropyl)-3-n-hexylurea (57.0 g; 86% yield) as colorless crystals, m.p. 48°-50° C.

Source