Iodine → HCID 85738089, compound

Participants

Reaction Steps

To metal magnesium, there was added methanol in an amount sufficient for immersing the magnesium metal and then a small amount of iodine powder was added thereto, under an argon gas atmosphere. The mixture was allowed to stand till foaming was initiated and then stirred till the color of the iodine disappeared. To the mixed liquid, there were added 3.00 g of 5-(1-benzylindol-4-yl)methylene-2,4-thiazolidinedione prepared in Example 2 and 210 ml of methanol, followed by stirring at room temperature and addition of 4.36 g of magnesium powder over 2 hours. After the addition of the magnesium powder, the resulting mixture was stirred at room temperature for 2 hours. The reaction solution was poured into 2 l of a 20% ammonium chloride aqueous solution, followed by extraction with dichloromethane (1 l×3). The resulting extract was washed with a 10% citric acid aqueous solution and a saturated common salt solution in this order, followed by drying the extract over anhydrous sodium sulfate and evaporation of the solvent under reduced pressure to give 2.24 g of 5-(1-benzylindol-4-yl)methyl-2,4-thiazolidinedione as yellow crystals. The yield thereof was found to be 74%.

Provenance & Evidence