Iodine → HCID 12968204, compound

HRID 885930Notes

Reaction equation

HRID 885930 reaction equation
Cl.[CH3:2][S:3]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)(=[O:5])=[O:4].CC([O-])(C)C.[K+].[I:19]I>CCO.S([O-])([O-])(=O)=O.[Ag+2]>[I:19][C:11]1[CH:12]=[C:6]([S:3]([CH3:2])(=[O:4])=[O:5])[CH:7]=[CH:8][C:9]=1[NH2:10]

Participants

6

Reactant 3

HCID 807IodineHCID 27351804-(Methylsulfonyl)aniline hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 12968204HCID 12968204, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent2×

Procedure

To a stirred suspension of 4-(methylsulfonyl)aniline hydrochloride (2.0 g, 9.7 mmol) in EtOH (40 mL) was added KOtBu (1.3 g, 11.4 mmol). The reaction mixture was stirred for 15 minutes, then a slurry of silver sulfate (3.3 g, 10.6 mmol) and iodine (2.4 g, 9.6 mmol) in EtOH (100 mL) was added. The reaction mixture was stirred at 50° C. for 3 h, then cooled to r.t., filtered through Celite®, and the filtrate concentrated in vacuo. Recrystallisation from EtOH gave the title compound (1.9 g, 66%) as an off-white solid. LCMS (ES+) 319.8 (M+Na)+, RT 2.77 minutes (Method 5).

Workup

  1. stirringThe reaction mixture was stirred at 50° C. for 3 h
  2. filtrationfiltered through Celite®
  3. concentrationthe filtrate concentrated in vacuo
  4. customRecrystallisation from EtOH

Sources & evidence

ORD record
ord-4307f3caa9044ed7ba6949eefa0003df
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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