N,N-Bis(2-hydroxyethyl)ethylenediamine → 1,1-dioctadecyl-3-{2-[Bis(2-Hydroxyethyl)Amino]Ethyl}Urea

HRID 371786Notes

Reaction equation

HRID 371786 reaction equation
[CH2:1]([N:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:20](Cl)=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH:41][CH2:42][CH2:43][N:44]([CH2:48][CH2:49][OH:50])[CH2:45][CH2:46][NH2:47]>C1C=CC=CC=1>[CH2:1]([N:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:20]([NH:47][CH2:46][CH2:45][N:44]([CH2:48][CH2:49][OH:50])[CH2:43][CH2:42][OH:41])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 98535N,N-Bis(2-hydroxyethyl)ethylenediamineHCID 3016265N,N-dioctadecylcarbamoyl chloride

Product 1

HCID 204330001,1-dioctadecyl-3-{2-[Bis(2-Hydroxyethyl)Amino]Ethyl}UreaYield 95.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of N,N-dioctadecylcarbamyl chloride (2.9 g.), N,N-bis-(2-hydroxyethyl)-1,2-ethanediamine (4.0 g.) and benzene (50 ml.) is refluxed and stirred for three hours. The mixture is then cooled, concentrated in vacuo and the residue taken up on chloroform (100 ml.). The chloroform solution is washed successively with water (2 × 50 ml.), aqueous sodium hydroxide (1 × 50 ml. of 1N) and water (2 × 50 ml.), then dried (Na2SO4). Removal of the chloroform in vacuo leaves the crude product as an oil (3.3 g.).

Workup

  1. temperatureis refluxed
  2. temperatureThe mixture is then cooled
  3. concentrationconcentrated in vacuo
  4. washThe chloroform solution is washed successively with water (2 × 50 ml.), aqueous sodium hydroxide (1 × 50 ml. of 1N) and water (2 × 50 ml.)
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the chloroform in vacuo

Sources & evidence

ORD record
ord-ea5b2b4d330443f19ba455c8fb291c2f
Source dataset
uspto-grants-1978_05
Patent number
US04087552

Reaction notes

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