Pyridine → HCID 14999110, compound

HRID 1030559Notes

Reaction equation

HRID 1030559 reaction equation
N1C=CC=CC=1.[OH:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[CH:13]([CH3:16])[S:12][CH:11]1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:23]([O:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[CH:13]([CH3:16])[S:12][CH:11]1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)(=[O:25])[CH3:24]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14999089HCID 14999089, compound

Product 1

HCID 14999110HCID 14999110, compoundYield 77%

Procedure

Pyridine (0.5 ml) was added to a solution of 3-(2-hydroxyethyl)-5-methyl-2-(3-pyridyl)thiazolidin-4-one (0.5 g, 2.1 mmol) in acetic anhydride (2 ml) under cooling with ice. This cooling with ice was further continued for 2 hours. The product mixture was concentrated by evaporation under reduced pressure, and subjected to medium-pressure chromatography (hexaneacetone), giving 3-(2-acetoxyethyl)-5-methyl-2-(3-pyridyl)thiazolidin-4-one (0.45 g, 77% yield). NMR (CDCl3) δ [ppm]; 1.62 (1 H, d, J=7.1 Hz), 1.66 (2 H, d, J=7.1 Hz), 2.06 (3 H, s), 5.74 (1 H, s). IR (CHCl3) [cm-1 ]; 2960, 1740, 1693, 1590, 1579, 1350, 1020.

Workup

  1. temperatureunder cooling with ice
  2. concentrationThe product mixture was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-467b97726e59433d8f2f93b480a56144
Source dataset
uspto-grants-1992_04
Patent number
US05106860

Reaction notes

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