Water → 1,2-bis(N-(2-hydroxyethyl)-palmitoylamino)ethane

HRID 1107607Notes

Reaction equation

HRID 1107607 reaction equation
[O-2:1].[Mg+2].O.[OH:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][OH:13].[C:14](Cl)(=[O:30])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O1CCOCC1>[OH:4][CH2:5][CH2:6][N:7]([C:29](=[O:1])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])[CH2:8][CH2:9][N:10]([C:14](=[O:30])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:11][CH2:12][OH:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8206Palmitoyl chlorideHCID 78179Ethanol, 2,2'-(1,2-ethanediyldiimino)bis-HCID 6850729Magnesium monoxide

Product 1

HCID 187877171,2-bis(N-(2-hydroxyethyl)-palmitoylamino)ethaneYield 78.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into other 500 ml rounded-flask, were introduced 4.0 g of magnesium oxide and 80 g of distilled water. The mixture was stirred. Thereto was added 7.3 g of N,N'-bis(2-hydroxyethyl)-1,2-diaminoethane prepared above and 250 ml of 1,4-dioxane. 27.5 g of palmitoyl chloride was gradually added dropwise to the resulting mixture for 1 hour under violent stirring at a room temperature. After stirring for 2 hours, the mixture was filtered, and then the filtrate was mixed with 200 ml of chloroform and washed twice with 200 ml of distilled water. Organic phase was cooled to produce solid material, which was recovered by filtration. The solid material was dried and recrystallized from chloroform/acetone and chloroform/hexane, to give 24.3 g of the title compound as white powder, which was identified by IR and NMR. The results are shown in Table 3.

Workup

  1. stirringunder violent stirring at a room temperature
  2. stirringAfter stirring for 2 hours
  3. filtrationthe mixture was filtered
  4. additionthe filtrate was mixed with 200 ml of chloroform
  5. washwashed twice with 200 ml of distilled water
  6. temperatureOrganic phase was cooled
  7. customto produce solid material, which
  8. filtrationwas recovered by filtration
  9. customThe solid material was dried
  10. customrecrystallized from chloroform/acetone and chloroform/hexane

Sources & evidence

ORD record
ord-97d7a9069a884906b67ef0bf2caf9e92
Source dataset
uspto-grants-2000_05
Patent number
US06060612

Reaction notes

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