Iodine → HCID 67384497, compound

HRID 1471872Notes

Reaction equation

HRID 1471872 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[I-:13].[Na+].II.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[I:13][C:4]1[C:3]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[C:2]([CH3:1])[NH:6][N:5]=1

Participants

7

Reactant 4

HCID 807IodineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1396013-Methyl-4-phenylpyrazol

Product 1

HCID 67384497HCID 67384497, compoundYield 27.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methyl-4-phenyl-1H-pyrazole (5.0 g, 31.6 mmol) in THF (40 mL) and water (40 mL) were added sodium iodide (4.74 g, 31.6 mmol), iodine (12.03 g, 47.4 mmol), and K2CO3 (4.37 g, 31.6 mmol) at room temperature. The reaction was refluxed for 2 h and then quenched with aqueous Na2SO3 (10%). The mixture was extracted with ethyl acetate, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless oil (2.5 g). LCMS m/z=284.7 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.26 (s, 3H), 7.24-7.54 (m, 5H), 13.13 (s, 1H).

Workup

  1. temperatureThe reaction was refluxed for 2 h
  2. customquenched with aqueous Na2SO3 (10%)
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-298c07162ad14947b72176e767f0daa0
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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