Acetyl chloride → N-(2,3-dihydroxypropyl)-N-(hexadecyl)ethanamide

HRID 2260079

Reaction equation

HRID 2260079 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][CH:6]([CH2:25][OH:26])[CH2:7][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(Cl)(Cl)Cl>[OH:5][CH:6]([CH2:25][OH:26])[CH2:7][N:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:1](=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 1110073-(Hexadecylamino)propane-1,2-diol

Product 1

HCID 18999304N-(2,3-dihydroxypropyl)-N-(hexadecyl)ethanamideYield 26%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Acetyl chloride (1.15g. 14.8 mmoles) was added dropwise to a reactor containing N-(2,3-dihydroxypropyl)-hexadecylamine (1.5 g, 4.3 mmoles) in 3 mL of chloroform. The reaction was stirred for 16 hours at room temperature. When the reaction was completed, the, mixture was concentrated, ethanol and water was added, and the pH of the reaction was adjusted to 14. This mixture was extracted with chloroform, and organic layer was collected and concentrated. The sample was purified on a silica column chromatography to give 0.4 g of product.

Workup

  1. concentrationthe, mixture was concentrated
  2. additionethanol and water was added
  3. extractionThis mixture was extracted with chloroform, and organic layer
  4. customwas collected
  5. concentrationconcentrated
  6. customThe sample was purified on a silica column chromatography

Sources & evidence

ORD record
ord-8281afeacc564c11883c03f614970d5d
Source dataset
uspto-grants-1995_12
Patent number
US05476661

Linked notes

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