Iodine → HCID 178434569, compound

HRID 1471935Notes

Reaction equation

HRID 1471935 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:3]=1.[I-:13].[Na+].II.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[I:13][C:3]1[C:2]([CH3:1])=[N:6][NH:5][C:4]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 807IodineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 187741H-Pyrazole,3-methyl-5-phenyl-

Product 1

HCID 178434569HCID 178434569, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-methyl-3-phenyl-1H-pyrazole (1.5 g, 9.48 mmol) in THF (20 mL) and water (20 mL), were added sodium iodide (1.42 g, 9.48 mmol), iodine (3.61 g, 14.22 mmol), and K2CO3 (1.96 g, 14.22 mmol) at room temperature. The reaction was warmed to 100° C. and stirred for 10 h. After cooling to room temperature, the reaction was poured into water and extracted with ethyl acetate, which was washed with 2.0 M aq. sodium thiosulfite and saturated. NaHCO3 successively. The extract was dried over MgSO4 and concentrated under reduced pressure to give a semi-solid, which was recrystallized from 10% ethyl acetate in hexane to give the title compound (1.9 g). LCMS m/z=285.5 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate, which
  3. washwas washed with 2.0 M aq. sodium thiosulfite
  4. dry with materialThe extract was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a semi-solid, which
  7. customwas recrystallized from 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5201ecd22ade42c9bc5f53929ed4b513
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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