Sodium Iodide → 4-Iodomethyl-2-(4-isopropylphenyl)-5-methyloxazole

HRID 748032Notes

Reaction equation

HRID 748032 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[I-:18].[Na+].C(OC)(C)(C)C>CC(C)=O>[I:18][CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 15413tert-Butyl methyl etherHCID 219742554-(Chloromethyl)-2-(4-isopropylphenyl)-5-methyloxazole

Product 1

HCID 574345184-Iodomethyl-2-(4-isopropylphenyl)-5-methyloxazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.74 g of 4-Chloromethyl-5-methyl-2-(4-(2-propyl)-phenyl)-oxazole 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 2.64 g of 4-iodomethyl-5-methyl-2-(4-(2-propyl)-phenyl)-oxazole as a yellowish solid. C14H16INO (341.19), MS(ESI): 342 (M+H+).

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-406dec4782c642c889761dd3411c62dd
Source dataset
uspto-grants-2008_07
Patent number
US07399777B2

Reaction notes

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