Stearoyl chloride → 5-Chloro-2,4-distearoyloxypyridine

HRID 466108Notes

Reaction equation

HRID 466108 reaction equation
[Cl:1][C:2]1[C:3]([OH:9])=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[C:10](Cl)(=[O:28])[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][CH2:24][CH2:25][CH2:26][CH3:27]>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([O:9][C:10](=[O:28])[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][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:4][C:5]([O:8][C:10](=[O:28])[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][CH2:24][CH2:25][CH2:26][CH3:27])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 8212Stearoyl chlorideHCID 54679224Gimeracil

Product 1

HCID 140495935-Chloro-2,4-distearoyloxypyridineYield 15%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 2.00 g quantity of 5-chloro-4-hydroxy-2-pyridone was refluxed in 150 ml of pyridine to obtain a uniform solution. To the solution was added 5.85 g of stearoyl chloride and the mixture was subjected to reaction at room temperature overnight. After completion of the reaction, the pyridine was concentrated and the concentrate was extracted with petroleum ether. The petroleum ether layer was concentrated and subjected to silica gel column chromatography using as an eluent petroleum ether-chloroform (1:9), giving 1.40 g of the title compound in a yield of 15%.

Workup

  1. customto obtain a uniform solution
  2. customthe mixture was subjected to reaction at room temperature overnight
  3. customAfter completion of the reaction
  4. concentrationthe pyridine was concentrated
  5. extractionthe concentrate was extracted with petroleum ether
  6. concentrationThe petroleum ether layer was concentrated

Sources & evidence

ORD record
ord-8cb6d0aa5054446d91fa4712be2634ed
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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