Thiazolidinedione → 5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione

Participants

Reaction Steps

In 1.1 liter of ethanol was dissolved 94 g of 4-[2(5-ethyl-2-pyridyl) ethoxy]benzaldehyde (content 80.6%) obtained by substantially the same manner as b) of Example 1. To the solution were added 93.7 g of 2,4-thiazolidinedione and 19.7 g of piperidine, and the mixture was stirred for 5 hours under reflux. The reaction mixture was gradually cooled to room temperature. Resulting crystals were collected by filtration under reduced pressure, washed with 100 ml of ethanol and dried at 50° C. under reduced pressure to give 77.1 g of 5-[4-[2-(5-ethyl-2-pyridyl)ethoxy]benzilidene]-2,4-thiazolidinedione as pale yellow crystals (content 99.5%). [The yield based on 4-[2-(5-ethyl-2-pyridyl) ethoxy]benzaldehyde was 73.0%.] This product was in complete agreement with the authentic sample, 5-[4-[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene]-2,4-thiazolidinedione, in various spectrum data.

Provenance & Evidence