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

HRID 1380197Notes

Reaction equation

HRID 1380197 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-2ddb5a103ba44923b1155c7c37ed4d7b
Source dataset
uspto-grants-1986_04
Patent number
US04579947

Reaction notes

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