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

HRID 1107608Notes

Reaction equation

HRID 1107608 reaction equation
[O-2].[Mg+2].O.[OH:4][CH2:5][CH2:6][N:7]([C:31](=[O:47])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]CCCC)[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]CCCC)[CH2:11][CH2:12][OH:13].C(Cl)(=O)CCCCCCCCCCC>O1CCOCC1>[OH:4][CH2:5][CH2:6][N:7]([C:31](=[O:47])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[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][CH3:25])[CH2:11][CH2:12][OH:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8166Dodecanoyl chlorideHCID 6850729Magnesium monoxideHCID 187877171,2-bis(N-(2-hydroxyethyl)-palmitoylamino)ethane

Product 1

HCID 187877201,2-bis(N-(2-hydroxyethyl)-lauroylamino)ethaneYield 325.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into a 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 in Example 27, and then was added 250 ml of 1,4-dioxane. 21.3 g of lauroyl 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 the filtrate was mixed with 200 ml of chloroform, and washed twice with 200 ml of distilled water. The organic phase was cooled to produce solid material, which was recovered by filtration. The solid material was dried and recrystallized from acetone, to give 19.5 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. temperatureThe organic phase was cooled
  7. customto produce solid material, which
  8. filtrationwas recovered by filtration
  9. customThe solid material was dried
  10. customrecrystallized from acetone

Sources & evidence

ORD record
ord-82c25168522245a1818c752bb0139da9
Source dataset
uspto-grants-2000_05
Patent number
US06060612

Reaction notes

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