Iodine → HCID 68663406, compound

HRID 452799Notes

Reaction equation

HRID 452799 reaction equation
[CH3:1][NH:2][C:3]([NH:5][NH:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][CH:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=3)[C:13]=2[CH:25]=1)=[O:8])=S.[OH-].[Na+].[I-].[K+].[K+].I[I-]I.II>C(O)C.O.C(OCC)(=O)C.CN(C)C=O>[CH3:1][NH:2][C:3]1[O:8][C:7]([C:9]2[CH:10]=[CH:11][C:12]3[O:16][CH:15]=[C:14]([C:17]4[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=4)[C:13]=3[CH:25]=2)=[N:6][N:5]=1

Participants

9

Reactant 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 86640032HCID 86640032, compoundHCID 131730724HCID 131730724, compound

Product 1

HCID 68663406HCID 68663406, compoundYield 24.7%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-methyl-2-[[3-[4-(methylthio)phenyl]-1-benzofuran-5-yl]carbonyl]hydrazinecarbothioamide (0.58 g, 1.56 mmol) in ethanol (10 mL) was added 2 M sodium hydroxide to adjust to pH 9 at 0° C., and 5% potassium iodide-iodine aqueous solution was added at room temperature until the color of iodine started to remain. N,N-Dimethylformamide (10 mL) was added to the mixture, and the resulting mixture was stirred overnight at room temperature. Ethyl acetate and water were added to the reaction mixture, and insoluble material was removed by filtration. The filtrate was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=2/3-3/2) and recrystallized from hexane/tetrahydrofuran to give the title compound (0.13 g, yield 24%) as colorless crystals.

Workup

  1. customto adjust to pH 9 at 0° C.
  2. customwas removed by filtration
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=2/3-3/2)
  8. customrecrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-14fa443497d042388a47e3fe53d57d68
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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