Iodine → HCID 15152173, compound

HRID 1515361Notes

Reaction equation

HRID 1515361 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[I:13]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[I:13][C:11]1[C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[S:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 3303462-Methyl-4H-1-benzothiopyran-4-one

Product 1

HCID 15152173HCID 15152173, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

2-Methyl-4H-thiochromen-4-one (1.0 mmol, 176 mg), iodine (1.2 mmol, 305 mg) and ceric ammonium nitrate (1.1 mmol, 603 mg) were dissolved in acetonitrile (4.0 mL), and the solution was stirred under a nitrogen atmosphere at 60° C. for 4 hours. After the disappearance of the starting materials was confirmed by thin-layer chromatography, the reaction solution was poured into a solution of a 10% saturated aqueous sodium thiosulfate solution under ice-cooling to terminate the reaction. The organic substances were extracted with methylene chloride, the obtained organic layer was dried over magnesium sulfate, and the solvents were evaporated under reduced pressure. The residue was purified by silica gel column chromatography, and the title compound (0.79 mmol, 238 mg) was obtained in a 79% yield.

Workup

  1. temperaturecooling
  2. customto terminate
  3. customthe reaction
  4. extractionThe organic substances were extracted with methylene chloride
  5. dry with materialthe obtained organic layer was dried over magnesium sulfate
  6. customthe solvents were evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9ae06fa930394eeeaea8c12812f4bd6d
Source dataset
uspto-grants-2012_07
Patent number
US08222429B2

Reaction notes

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