Ethanolamine → HCID 14999112, compound

HRID 1030560Notes

Reaction equation

HRID 1030560 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.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1.[CH2:23]([CH2:25][NH2:26])[OH:24]>C1(C)C=CC=CC=1>[OH:24][CH2:23][CH2:25][N:26]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:15]1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 103713-PyridinecarboxaldehydeHCID 219323062-Sulfanylundecanoic acid

Product 1

HCID 14999112HCID 14999112, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Mercaptoundecanoic acid (7 g, 32.1 mmol), nicotinaldehyde (3.03 ml, 32.1 mmol), and ethanolamine (1.93 ml, 32.1 mmol) were added to toluene, (100 ml) and subjected to azeotropic dehydration for 1 hour. The product mixture was cooled and evaporated under reduced pressure to remove the solvent. The residue was purified by column chromatography, giving 3-(2-hydroxyethyl)-5-(n-nonyl)-2-(3-pyridyl)thiazolidin-4-one (8.17 g, 73% yield). NMR (CDCl3, δ) [ppm]; 0.85-0.9 (3 H, m), 2.9-3.01 (1 H, m), 3.65-3.80 (3 H, m), 3.97-4.01 (0.7 H, m), 4.02-4.07 (0.3 H, m), 5.78 (0.3 H, d, J=2.0 Hz), 5.80 (0.7 H, s).

Workup

  1. temperatureThe product mixture was cooled
  2. customevaporated under reduced pressure
  3. customto remove the solvent
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2f6d59766b3f46c68691fb7219e24116
Source dataset
uspto-grants-1992_04
Patent number
US05106860

Reaction notes

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