Iodine → HCID 178503595, compound

HRID 1471855Notes

Reaction equation

HRID 1471855 reaction equation
[CH3:1][S:2][C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=1.[I-:14].[Na+].II.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[I:14][C:4]1[C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:6][NH:7][C:3]=1[S:2][CH3:1]

Participants

7

Reactant 4

HCID 807IodineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 178503083HCID 178503083, compound

Product 1

HCID 178503595HCID 178503595, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-(methylthio)-3-phenyl-1H-pyrazole (1.5 g, 7.88 mmol) in THF (20 mL) and water (20 mL), were added sodium iodide (1.182 g, 7.88 mmol), iodine (3.00 g, 11.83 mmol), and K2CO3 (1.634 g, 11.83 mmol) at room temperature. The reaction was warmed to 100° C. and stirred for 2 h. The reaction was quenched with 2.0 M aqueous sodium thiosulfite and concentrated under reduced pressure. The mixture was extracted with ethyl acetate and washed with NaHCO3 solution. The organic extracts were dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (2.35 g). LCMS m/z=317.02 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.43 (s, 3H), 7.43-7.79 (m, 5H), 13.5 (s, 1H).

Workup

  1. customThe reaction was quenched with 2.0 M aqueous sodium thiosulfite
  2. concentrationconcentrated under reduced pressure
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with NaHCO3 solution
  5. dry with materialThe organic extracts were dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-492923d6a95b4316b7e7c24b8e8ebae4
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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