Iodine → HCID 12968204, compound

HRID 2187729Notes

Reaction equation

HRID 2187729 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[I:12]I>CCO.S([O-])([O-])(=O)=O.[Ag+2]>[I:12][C:9]1[CH:10]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[CH:7][C:8]=1[NH2:11]

Participants

5

Reactant 2

HCID 807Iodine2×HCID 796174-(Methylsulfonyl)aniline

Product 1

HCID 12968204HCID 12968204, compoundYield 242.6%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalyst2×HCID 702EthanolSolvent3×

Conditions

Temperature
0 °C

Procedure

To a vigorously stilted solution of 100 g of 4-(methylsulfonyl)-phenylamine dissolved in 5.5 L of EtOH at 50° C. was added a mixture of 49.3 g of iodine and 110 g of silver sulfate in 1 L of EtOH. This was repeated after 1 h of stirring. After another hour, a mixture of 49.3 g of iodine and 43.8 g of silver sulfate in 1 L of EtOH was added and the mixture stirred overnight. The hot solution was then filtered through Celite and the solvent stripped. The residue was triturated with 1 L of EtOH at 50° C. for 45 min and cooled to 0° C. The product was filtered and collected to give 140 g of the title compound as a brown solid.

Workup

  1. additionwas added
  2. waitAfter another hour
  3. additionwas added
  4. stirringthe mixture stirred overnight
  5. filtrationThe hot solution was then filtered through Celite
  6. customThe residue was triturated with 1 L of EtOH at 50° C. for 45 min
  7. filtrationThe product was filtered
  8. customcollected

Sources & evidence

ORD record
ord-f7727b9f83e5496db2eac50d3a8b6d33
Source dataset
uspto-grants-2002_06
Patent number
US06410583B1

Reaction notes

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