Hexane → 5-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole

HRID 1274311Notes

Reaction equation

HRID 1274311 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[CH:3]=1.[I:21]N1C(=O)CCC1=O.CCCCCC>C(#N)C>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:16])([F:15])[F:17])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[I:21]

Participants

5

Reactant 3

HCID 8058HexaneHCID 120273N-IodosuccinimideHCID 33039135-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile

Product 1

HCID 154620775-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (prepared as described in EP 295 117 A1) (5.0 g) in acetonitrile (60 ml) at room temperature was added N-iodosuccinimide (3.52 g), portionwise over a period of five minutes. Stirring was continued for 1 hr and the mixture was then evaporated to dryness to provide the crude product (8.2 g), still containing succinimide. This may be used without further purification or, if desired, purified by partitioning between dichloromethane and water, separating, drying (MgSO4) and evaporating the organic layer to produce a yellow solid. Trituration with hexane provided the title compound as a white solid, m.p. 213° C. (decomp.).

Workup

  1. waitwas continued for 1 hr
  2. customthe mixture was then evaporated to dryness
  3. customto provide the crude product (8.2 g), still containing succinimide
  4. customThis may be used without further purification
  5. custompurified
  6. customby partitioning between dichloromethane and water
  7. customseparating
  8. dry with materialdrying (MgSO4)
  9. customevaporating the organic layer
  10. customto produce a yellow solid

Sources & evidence

ORD record
ord-bb74f8f05ae24a389f013c7dd99f0cc3
Source dataset
uspto-grants-2000_12
Patent number
US06156782

Reaction notes

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