Palmitoyl chloride → HCID 86755404, compound

HRID 1107612Notes

Reaction equation

HRID 1107612 reaction equation
[O-2].[Mg+2].[OH:3][CH2:4][CH2:5][CH2:6][NH:7][CH2:8][CH:9]([OH:16])[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][OH:15].[C:17](Cl)(=[O:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[C:35](Cl)(=[O:53])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]/[CH:43]=[CH:44]\[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]>O1CCOCC1.O>[OH:3][CH2:4][CH2:5][CH2:6][N:7]([C:17](=[O:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:8][CH:9]([OH:16])[CH2:10][N:11]([CH2:12][CH2:13][CH2:14][OH:15])[C:35](=[O:53])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]/[CH:43]=[CH:44]\[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]

Participants

7

Reactant 4

HCID 8206Palmitoyl chlorideHCID 5364783Oleoyl chlorideHCID 6850729Magnesium monoxideHCID 18787698HCID 18787698, compound

Product 1

HCID 86755404HCID 86755404, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Into other 500 ml rounded-flask, 4.0 g of magnesium oxide and 80 g of distilled water were placed. While stirring resultant mixture, 10.4 g of N,N'-bis(3-hydroxypropyl)-2-hydroxy-1,3-propanediamine was added, and then was added 250 ml of 1,4-dioxane. 13.4 g of palmitoyl chloride was added portionwise to the resulting mixture over 1 hour under violent stirring at a room temperature. After stirring for 2 hours at 10° C., 14.7 g of oleoyl chloride was gradually added dropwise over 1 hour. After stirring again 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 4.

Workup

  1. additionwas added
  2. stirringAfter stirring for 2 hours at 10° C.
  3. stirringAfter stirring again 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-309322880e43496382107d75a6c0a999
Source dataset
uspto-grants-2000_05
Patent number
US06060612

Reaction notes

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