Pyridine → HCID 12790424, compound

HRID 1702880Notes

Reaction equation

HRID 1702880 reaction equation
[CH:1]([C:3]1[S:7][C:6]([N:8]([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:9](=[O:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1)=[O:2].N1C=CC=CC=1.[O-:35][Mn](=O)(=O)=O.[K+]>O>[CH2:13]([N:8]([C:9](=[O:12])[CH2:10][CH3:11])[C:6]1[S:7][C:3]([C:1]([OH:35])=[O:2])=[CH:4][CH:5]=1)[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]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 516875Potassium Permanganate2×HCID 12790419HCID 12790419, compound

Product 1

HCID 12790424HCID 12790424, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

57.8 g of N-(5-formyl-thien-2-yl)-N-hexadecyl-propionic acid amide are dissolved in 300 cc. of pyridine. A solution of 14.6 g of KMnO4 in 198 cc. of pyridine and 85 cc. of water is added with stirring and cooling such that the temperature of the reaction does not rise above -3° C. Stirring is continued until all of KMnO4 has been reacted. Thereafter, the solvent is distilled off, the residue is triturated with dillued acid and the mixture is extracted with chloroform. The chloroform layer is separated, washed with water and dried over Na2SO4. The solvent is evaporated and the resulting crude product is purified chromatographically on a column of silicic acid gel using chloroform as eluant.

Workup

  1. temperaturecooling such that the temperature of the reaction
  2. customdoes not rise above -3° C
  3. stirringStirring
  4. customhas been reacted
  5. distillationThereafter, the solvent is distilled off
  6. customthe residue is triturated with dillued acid
  7. extractionthe mixture is extracted with chloroform
  8. customThe chloroform layer is separated
  9. washwashed with water
  10. dry with materialdried over Na2SO4
  11. customThe solvent is evaporated
  12. customthe resulting crude product is purified chromatographically on a column of silicic acid gel

Sources & evidence

ORD record
ord-459bd8a975524e02aaa0453a81a67e59
Source dataset
uspto-grants-1982_09
Patent number
US04349686

Reaction notes

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