Palmitoyl chloride → N,N'-bis(2-hydroxyethyl)-N-palmitoyl-N'-oleoyl-1,2-diaminoethane

HRID 1107609Notes

Reaction equation

HRID 1107609 reaction equation
[O-2].[Mg+2].[OH:3][CH2:4][CH2:5][N:6]([C:30](=[O:46])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:7][CH2:8][N:9]([C:13](=[O:29])[CH2:14][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][CH3:28])[CH2:10][CH2:11][OH:12].[C:47](Cl)(=O)[CH2:48]CCCCCCCCCCCCCC.C(Cl)(=O)CCCCCCC/C=C\CCCCCCCC>O1CCOCC1.O>[OH:3][CH2:4][CH2:5][N:6]([C:30](=[O:46])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:7][CH2:8][N:9]([CH2:10][CH2:11][OH:12])[C:13](=[O:29])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:47][CH3:48]

Participants

7

Reactant 4

HCID 8206Palmitoyl chlorideHCID 5364783Oleoyl chlorideHCID 6850729Magnesium monoxideHCID 187877171,2-bis(N-(2-hydroxyethyl)-palmitoylamino)ethane

Product 1

HCID 86755402N,N'-bis(2-hydroxyethyl)-N-palmitoyl-N'-oleoyl-1,2-diaminoethaneYield 348.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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. 13.4 g of palmitoyl chloride was gradually added dropwise to the resulting mixture for 1 hour under violent stirring at 10° C. After stirring for 2 hours at 10° C., 14.7 g of oleoyl chloride was gradually added dropwise thereto for 1 hour. 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. 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 26.5 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 10° C
  2. stirringAfter stirring for 2 hours at 10° C.
  3. stirringAfter stirring for 2 hours
  4. filtrationthe mixture was filtered
  5. additionthe filtrate was mixed with 200 ml of chloroform
  6. washwashed twice with 200 ml of distilled water
  7. temperatureThe organic phase was cooled
  8. customto produce solid material, which
  9. filtrationwas recovered by filtration
  10. customThe solid material was dried
  11. customrecrystallized from acetone

Sources & evidence

ORD record
ord-0a2da7d39cb44720a19dcb2a7f598bb2
Source dataset
uspto-grants-2000_05
Patent number
US06060612

Reaction notes

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