Acetonitrile → HCID 67207288, compound

HRID 1253479Notes

Reaction equation

HRID 1253479 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[CH:5][CH:4]=1)[CH3:2].[I:14]N1C(=O)CCC1=O.C(#N)C>C(OCC)(=O)C>[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[CH:5][C:4]=1[I:14])[CH3:2]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 120273N-IodosuccinimideHCID 12529302HCID 12529302, compound

Product 1

HCID 67207288HCID 67207288, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

5-ethyl-1-phenyl-1H-pyrazole (21 mg, 0.12 mmol) and N-iodosuccinimide (41 mg, 0.18 mmol) were added to acetonitrile (5 ml). The reaction mixture was heated to 60° C. After 1 hour, 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 5-ethyl-4-iodo-1-phenyl-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-421b12a6bb6340fe95355bd7fa75c5f6
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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