Iodine → HCID 85738089, compound

HRID 2394392Notes

Reaction equation

HRID 2394392 reaction equation
[Mg].II.[CH2:4]([N:11]1[C:19]2[C:14](=[C:15]([CH:20]=[C:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[NH4+]>CO>[CH2:4]([N:11]1[C:19]2[C:14](=[C:15]([CH2:20][CH:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 807Iodine2×HCID 25517Ammonium ChlorideHCID 5462224Magnesium4×HCID 54151686HCID 54151686, compound

Product 1

HCID 85738089HCID 85738089, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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%.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. extractionfollowed by extraction with dichloromethane (1 l×3)
  3. extractionThe resulting extract
  4. washwas washed with a 10% citric acid aqueous solution
  5. customby drying the
  6. extractionextract over anhydrous sodium sulfate and evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-9c3148494c6f4e40a09ff871de9b15ba
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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