Pyridine → HCID 12790423, compound

HRID 1702879Notes

Reaction equation

HRID 1702879 reaction equation
[CH:1]([C:3]1[S:7][C:6]([N:8]([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])[C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1)=[O:2].N1C=CC=CC=1.[Mn]([O-])(=O)(=O)=[O:35].[K+]>O>[C:9]([N:8]([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])[C:6]1[S:7][C:3]([C:1]([OH:35])=[O:2])=[CH:4][CH:5]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 516875Potassium Permanganate2×HCID 12790418HCID 12790418, compound

Product 1

HCID 12790423HCID 12790423, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

25 g of N-(5-formyl-thien-2-yl)-N-hexadecylacetamide are dissolved in 20 cc. of pyridine. A solution of 6.7 g of potassium permanganate in 90 cc. of pyridine and 40 cc. of water is added with stirring and cooling such that the temperature of the reaction mixture does not rise above -3° C. Stirring is continued until all of KMnO4 has been reacted. Thereafter, the solvents are distilled off, the residue is triturated with dilute hydrochloric 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 mixture
  2. customdoes not rise above -3° C
  3. stirringStirring
  4. customhas been reacted
  5. distillationThereafter, the solvents are distilled off
  6. customthe residue is triturated with dilute hydrochloric 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-d09b2755d5d8446e92c1a286a2bd3967
Source dataset
uspto-grants-1982_09
Patent number
US04349686

Reaction notes

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