Sodium Iodide → 5-(Iodomethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole

HRID 854570Notes

Reaction equation

HRID 854570 reaction equation
Cl[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH3:18].[Na+].[I-:20]>CC(C)=O>[I:20][CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH3:18]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole

Product 1

HCID 236145065-(Iodomethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazoleYield 102.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (0.51 g, 1.73 mmol) in acetone is added NaI (0.42 g, 2.80 mmol). The mixture is stirred at RT for 3 h. The solid is filtered, and the filtrate is concentrated. The resulting solid is washed with Et2O and refiltered. Concentration of the filtrate yielded the title compound (0.68 g, quant.). The material is used without further purification.

Workup

  1. filtrationThe solid is filtered
  2. concentrationthe filtrate is concentrated
  3. washThe resulting solid is washed with Et2O

Sources & evidence

ORD record
ord-ab173c29cfbf40cb9fd395cf86f8eae5
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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