Sodium Iodide → 4-Iodomethyl-5-methyl-2-naphthalen-2-yloxazole

HRID 1373159Notes

Reaction equation

HRID 1373159 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)[O:6][C:7]=1[CH3:8].[I-:19].[Na+].C(OC)(C)(C)C>CC(C)=O>[I:19][CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)[O:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 15413tert-Butyl methyl etherHCID 121580734-(Chloromethyl)-5-methyl-2-(naphthalen-2-yl)-1,3-oxazole

Product 1

HCID 210742684-Iodomethyl-5-methyl-2-naphthalen-2-yloxazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.8 g of 4-chloromethyl-5-methyl-2-naphthalen-2-yloxazole and 3 g of sodium iodide in 150 ml of acetone are heated under reflux for 2 hours. After the reaction mixture has been cooled, 300 ml of methyl tert-butyl ether are added, the mixture is washed three times with saturated Na2S2O3 solution and dried over MgSO4 and the solvents are then removed under reduced pressure. This gives 2.7 g of 4-iodomethyl-5-methyl-2-naphthalen-2-yloxazole as a light-yellow solid.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter the reaction mixture has been cooled
  3. washthe mixture is washed three times with saturated Na2S2O3 solution
  4. dry with materialdried over MgSO4
  5. customthe solvents are then removed under reduced pressure

Sources & evidence

ORD record
ord-fd05c981796b448b8502a53815ae871b
Source dataset
uspto-grants-2007_01
Patent number
US07160911B2

Reaction notes

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