3-Pyridinecarboxaldehyde → HCID 14999116, compound

HRID 1030562Notes

Reaction equation

HRID 1030562 reaction equation
[SH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:3]([OH:5])=O.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=O)[CH:16]=1.[CH3:23][N:24]([CH2:26][CH2:27][NH2:28])[CH3:25]>C1(C)C=CC=CC=1>[CH3:23][N:24]([CH3:25])[CH2:26][CH2:27][N:28]1[C:3](=[O:5])[CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[S:1][CH:21]1[C:17]1[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 66053N,N-DimethylethylenediamineHCID 219323062-Sulfanylundecanoic acid

Product 1

HCID 14999116HCID 14999116, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Mercaptoundecanoic acid (5.0 g, 22.9 mmol), pyridine-3-aldehyde (2.16 ml, 22.9 mmol), and N-dimethylaminoethylamine (2.51 ml, 22.9 mmol) were dissolved in toluene (100 ml), and subjected to azeotropic dehydration for 2 hours. The solvent was removed from the product mixture by evaporation under reduced pressure. The residue was purified by column chromatography, giving 3-(2-dimethylaminoethyl)-5-(n-nonyl)-2-(3-pyridyl)thiazolidin-4-one (7.9 g, 91% yield). IR (CHCl3) [cm-1 ]; 2850, 1660, 1577, 1408.

Workup

  1. customThe solvent was removed from the product mixture by evaporation under reduced pressure
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-36074f6c9df34a33b23f766897770239
Source dataset
uspto-grants-1992_04
Patent number
US05106860

Reaction notes

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