N-Iodosuccinimide → HCID 22645651, compound

HRID 2287414Notes

Reaction equation

HRID 2287414 reaction equation
[NH2:1][C:2]1[N:3]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[Cl:20])[CH:4]=[C:5]([C:7]#[N:8])[CH:6]=1.[I:21]N1C(=O)CCC1=O>C(#N)C.O>[NH2:1][C:2]1[N:3]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:17])[F:18])=[CH:11][C:10]=2[Cl:20])[CH:4]=[C:5]([C:7]#[N:8])[C:6]=1[I:21]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 22645636HCID 22645636, compound

Product 1

HCID 22645651HCID 22645651, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-cyanopyrrole (EP-372982 A2) in acetonitrile (20 ml) was added N-iodosuccinimide (703 mg). The reaction was stirred at room temperature for 30 minutes, diluted with water (100 ml) and extracted with ether (100 ml). The organic fraction was separated, dried over MgSO4, filtered and evaporated to dryness, the residue was purified by column chromatography (silica, 20 g) eluted with dichloromethane:hexane (7:3) to give the title compound as a yellow crystaline material, m.p. 130-132° C.

Workup

  1. extractionextracted with ether (100 ml)
  2. customThe organic fraction was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customthe residue was purified by column chromatography (silica, 20 g)
  7. washeluted with dichloromethane:hexane (7:3)

Sources & evidence

ORD record
ord-3b101629b4ce4cbc8fd637305e3d81d6
Source dataset
uspto-grants-2000_07
Patent number
US06083965

Reaction notes

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