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

HRID 2301386Notes

Reaction equation

HRID 2301386 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>C(Cl)(Cl)(Cl)Cl>[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

4

Reactant 2

HCID 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]pyrazoleYield 29.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile (9.8 g) and N-iodosuccinimide (8.87 g) was heated at reflux in carbon tetrachloride for 3.5 hours, cooled and washed with sodium bisulfite solution, NaOH solution and water. The dried (magnesium sulfate) solution was evaporated and purified by chromatography on silica gel eluting with dichloromethane to give 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-iodo-1H-pyrazole-3-carbonitrile (4.0 g), m.p.212-214° C.

Workup

  1. temperaturewas heated
  2. temperaturecooled
  3. washwashed with sodium bisulfite solution, NaOH solution and water
  4. dry with materialThe dried (magnesium sulfate) solution
  5. customwas evaporated
  6. custompurified by chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-f5a43ae390774573a0d86e97d9a1c8aa
Source dataset
uspto-grants-2002_12
Patent number
US06500850B2

Reaction notes

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