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Acetonitrile → 5-cyclopropyl-4-iodo-1-phenyl-1H-pyrazole

HRID 1253483
Notes
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Reaction equation

HRID 1253483 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[I:15]N1C(=O)CCC1=O.C(#N)C>C(OCC)(=O)C>[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:7]=[CH:6][C:5]=2[I:15])[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 120273N-IodosuccinimideHCID 672067065-cyclopropyl-1-phenyl-1H-pyrazole

Product 1

HCID 672072835-cyclopropyl-4-iodo-1-phenyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

5-cyclopropyl-1-phenyl-1H-pyrazole (200 mg, 1.09 mmol) and N-iodosuccinimide (366 mg, 1.63 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 5-cyclopropyl-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-3c4a40280afd47c588d4e7037fe3d4d9
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08455477B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes