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

HRID 1767891Notes

Reaction equation

HRID 1767891 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].[I-:19].[Na+]>CC(C)=O>[I:19][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 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole [4 g, 13.7 mmol; PCT Int. Appl. (2002), WO 0262774 A1] and sodium iodide (10.3 g, 68.6 mmol) in acetone (70 ml) was stirred at reflux temperature for 2 h under an argon atmosphere. The yellow precipitate was filtered off, the filtrate evaporated to dryness under reduced pressure and dissolved in tert-butyl methyl ether and brine/ice water 1/1. The aqueous layer was extracted one more time with tert-butyl methyl ether, the combined extracts washed with ice water/aqueous sodium thiosulfate, ice water/brine 1/1 and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue recrystallized from tert-butyl methyl ether/heptane to give 2.5 g (6.5 mmol, 48%) of the title compound as yellow crystals.

Workup

  1. temperatureat reflux temperature for 2 h under an argon atmosphere
  2. filtrationThe yellow precipitate was filtered off
  3. customthe filtrate evaporated to dryness under reduced pressure
  4. dissolutiondissolved in tert-butyl methyl ether
  5. extractionThe aqueous layer was extracted one more time with tert-butyl methyl ether
  6. washthe combined extracts washed with ice water/aqueous sodium thiosulfate, ice water/brine 1/1
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe residue recrystallized from tert-butyl methyl ether/heptane

Sources & evidence

ORD record
ord-e85330436dc845c68eb7d88b2fba1fd0
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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