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

HRID 377643Notes

Reaction equation

HRID 377643 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 (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 provides 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-3318911842104b2e967b51ec08db080e
Source dataset
uspto-grants-2000_02
Patent number
US06028096

Reaction notes

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