Iodine → HCID 12968204, compound

HRID 988671Notes

Reaction equation

HRID 988671 reaction equation
[I:1]I.[CH3:3][S:4]([C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1)(=[O:6])=[O:5]>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[I:1][C:12]1[CH:13]=[C:7]([S:4]([CH3:3])(=[O:5])=[O:6])[CH:8]=[CH:9][C:10]=1[NH2:11]

Participants

5

Reactant 2

HCID 807IodineHCID 796174-(Methylsulfonyl)aniline

Product 1

HCID 12968204HCID 12968204, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of iodine (20.8 g, 81.8 mmol) and silver sulfate (25.5 g, 81.8 mmol) in ethanol (1 L) was added 4-(methylsulfonyl)aniline (14 g, 81.8 mmol). After stirring overnight, the solution was filtered. The precipitate was then suspended in THF and stirred for 48 h, then filtered again and the filtrate was concentrated in vacuo to give 15.5 g (64%) of tan solid. The original filtrate was also concentrated in vacuo and then suspended in ethanol with stirring, then filtered and dried in vacuo to give another 7.92 g (33%) of tan solid.

Workup

  1. filtrationthe solution was filtered
  2. stirringstirred for 48 h
  3. filtrationfiltered again
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5f07ee171f054cdfb83820be104ef639
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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