Acetonitrile → HCID 67207269, compound

HRID 1253486Notes

Reaction equation

HRID 1253486 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[N:5]=[CH:4][CH:3]=1.[I:12]N1C(=O)CCC1=O.C(#N)C>C(OCC)(=O)C>[I:12][C:9]1[S:8][C:7]([N:6]2[C:2]([CH3:1])=[CH:3][CH:4]=[N:5]2)=[CH:11][CH:10]=1.[I:12][C:3]1[CH:4]=[N:5][N:6]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 120273N-IodosuccinimideHCID 67207277HCID 67207277, compound

Product 2

HCID 67207269HCID 67207269, compoundHCID 67207339HCID 67207339, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

5-methyl-1-(2-thienyl)-1H-pyrazole (64 mg, 0.39 mmol) and N-iodosuccinimide (88 mg, 0.39 mmol) were added to acetonitrile (5 ml). The reaction mixture was heated to 70° C. After 6 hours, the reaction mixture was diluted with ethyl acetate, washed with 1N aqueous sodium hydroxide and brine, then dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/hexanes gradient) to afford 1-(5-iodo-2-thienyl)-5-methyl-1H-pyrazole and 4-iodo-5-methyl-1-(2-thienyl)-1H-pyrazole.

Workup

  1. washwashed with 1N aqueous sodium hydroxide and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-a6e1e37e115d420b82807831f1afb13c
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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