P-Toluenesulfonamide → N-tosyliminophenyliodinane

HRID 252222Notes

Reaction equation

HRID 252222 reaction equation
C(O[C:5]1[C:6](OC(=O)C)=[C:7]([I:11])[CH:8]=[CH:9][CH:10]=1)(=O)C.[OH-].[K+].[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:23][CH:24]=1>CO>[C:19]1([CH3:18])[CH:20]=[CH:21][C:22]([S:25]([N:28]=[C:7]2[CH2:6][CH2:5][CH2:10][CH2:9][I:11]2[C:7]2[CH:6]=[CH:5][CH:10]=[CH:9][CH:8]=2)(=[O:27])=[O:26])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6269P-ToluenesulfonamideHCID 14797Potassium HydroxideHCID 21865429Bis(acetoxy)iodobenzene

Product 1

HCID 86611515N-tosyliminophenyliodinaneYield 113.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Diacetoxyiodobenzene (12.88 g, 40 mmol) was added to a solution of KOH (5.61 g, 100 mmol) and p-toluenesulfonamide (6.85 g, 40 mmol) in methanol (160 mL) at 8° C. A yellow color developed within 1 minute. The cooling bath was removed, and the solution was allowed to warm to RT with stirring for 3 hours. Water (180 mL) was added and the reaction was refrigerated overnight. The precipitate was collected by filtration and dried overnight in a vacuum dessicator to yield 10 g (66%) of a light yellow solid which was used with out further purification or characterization.

Workup

  1. customThe cooling bath was removed
  2. additionWater (180 mL) was added
  3. waitthe reaction was refrigerated overnight
  4. filtrationThe precipitate was collected by filtration
  5. customdried overnight in a vacuum dessicator

Sources & evidence

ORD record
ord-d3bd792dcf0f4539a355ce4befb7d585
Source dataset
uspto-grants-2011_01
Patent number
US07868023B2

Reaction notes

Loading…