Triethylamine → 1-(3-Chloropropyl)-3-n-hexylurea

HRID 543184Notes

Reaction equation

HRID 543184 reaction equation
C(N(CC)CC)C.Cl.[Cl:9][CH2:10][CH2:11][CH2:12][NH2:13].[CH2:14]([N:20]=[C:21]=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>C(Cl)Cl>[Cl:9][CH2:10][CH2:11][CH2:12][NH:13][C:21]([NH:20][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75659Hexyl isocyanateHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Product 1

HCID 136067321-(3-Chloropropyl)-3-n-hexylureaYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe residue was treated with ether
  3. filtrationthe colorless solid was filtered off
  4. washThe ether solution was then washed with water
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2e627a3b779940e7a096bbba2d2c5c27
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Reaction notes

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