Sodium Iodide → HCID 19422068, compound

HRID 744696Notes

Reaction equation

HRID 744696 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:7].[I-:19].[Na+].CCCCCC>CC(C)=O>[I:19][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:7]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8058Hexane2×HCID 15229344HCID 15229344, compound

Product 1

HCID 19422068HCID 19422068, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5--Chloro-N-[4--(trifluoromethyl)phenyl]-pentanamide (2.795 g) and sodium iodide (3.32 g) were stirred in acetone (20 ml) at 22° C. for 3d, then heated at reflux for 16h, all under nitrogen. The cooled reaction mixture was chromatographed with 50:50 ethyl acetate:hexane to isolate product with Rf =0.30 in 35:65 ethyl acetate:hexane by addition of hexane and evaporation of solvent under a stream of nitrogen afforded, after suction filtration, a white solid (2.8 87 g). The product iodide contained ca. 5% starting chloride and was used without further purification.

Workup

  1. temperatureheated
  2. customThe cooled reaction mixture
  3. customwas chromatographed with 50:50 ethyl acetate
  4. customhexane to isolate product with Rf =0.30 in 35:65 ethyl acetate
  5. customafforded
  6. filtrationafter suction filtration
  7. customwas used without further purification

Sources & evidence

ORD record
ord-fa2a0aab25134f1b85328e49cc540852
Source dataset
uspto-grants-1996_09
Patent number
US05559143

Reaction notes

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