Sodium Iodide → 2-(4-Methoxyphenyl)-4-iodomethyl-5-methyloxazole

HRID 2233556

Reaction equation

HRID 2233556 reaction equation
[I-:1].[Na+].Cl[CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[O:8][C:9]=1[CH3:10]>CC(C)=O>[I:1][CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[O:8][C:9]=1[CH3:10]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 144799554-(Chloromethyl)-2-(4-methoxyphenyl)-5-methyl-1,3-oxazole

Product 1

HCID 224936592-(4-Methoxyphenyl)-4-iodomethyl-5-methyloxazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Together with 37.7 g of sodium iodide, 19.9 g of 4-chloromethyl-2-(4-methoxy-phenyl)-5-methyl-oxazole are, in 300 ml of acetone, heated at the boil under reflux for 2 hours. After cooling of the reaction mixture, the solvent was removed under reduced pressure and the residue dissolved in 300 ml of methyl tert-butyl ether, the mixture is washed three times with saturated Na2S2O3 solution and dried over MgSO4, and the solvent is then removed under reduced pressure. This gives 49.8 g of 4-Iodomethyl-2-(4-methoxyphenyl)-5-methyloxazole as a light-brown solid.

Workup

  1. temperatureheated at the boil
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling of the reaction mixture
  4. customthe solvent was removed under reduced pressure
  5. dissolutionthe residue dissolved in 300 ml of methyl tert-butyl ether
  6. washthe mixture is washed three times with saturated Na2S2O3 solution
  7. dry with materialdried over MgSO4
  8. customthe solvent is then removed under reduced pressure

Sources & evidence

ORD record
ord-e918121f953b4191933a6f57c3dc45fc
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Linked notes

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