Hexanoyl chloride → HCID 18999305, compound

HRID 2260080Notes

Reaction equation

HRID 2260080 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH:9][CH:10]([CH2:29][OH:30])[CH2:11][NH:12][CH2:13][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]>C(Cl)(Cl)Cl>[OH:9][CH:10]([CH2:29][OH:30])[CH2:11][N:12]([CH2:13][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])[C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 67340Hexanoyl chlorideHCID 1110073-(Hexadecylamino)propane-1,2-diol

Product 1

HCID 18999305HCID 18999305, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Hexanoyl chloride (2.65g, 19.7 mmoles) was added dropwise to a reactor containing N-(2,3-dihydroxypropyl)-hexadecylamine (2.65g, 19.7 mmoles)in 8 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 crude sample was purified on silica column chromatography to give 1.56 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 crude sample was purified on silica column chromatography

Sources & evidence

ORD record
ord-889bd1ab51a340bc9c1000bbfc525480
Source dataset
uspto-grants-1995_12
Patent number
US05476661

Reaction notes

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