Hydrogen Peroxide → Trifluoromethyluracil

HRID 1363432Notes

Reaction equation

HRID 1363432 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].S(=O)(=O)(O)O.[F:14][C:15](I)([F:17])[F:16].OO>[Fe].CS(C)=O>[F:14][C:15]([F:17])([F:16])[C:7]1[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][CH:8]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 1174UracilHCID 16843Trifluoroiodomethane

Product 1

HCID 5899TrifluoromethyluracilYield 32%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
45 °C

Procedure

0.11 g (1.0 mmol) of uracil and 0.028 g (0.5 mmol) of iron powder were weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 2.0 ml of dimethyl sulfoxide, 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide and 0.2 ml of a 30% hydrogen peroxide aqueous solution. The mixture was stirred at 40 to 50° C. for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (19F-NMR yield: 32%) was confirmed in the same manner as in Example 1.

Workup

  1. customplaced in a 50 ml two-neck flask
  2. customequipped with a magnetic rotor
  3. additionThe following materials were added
  4. temperaturethe resulting solution was cooled to room temperature

Sources & evidence

ORD record
ord-c16cca55871e4df4b2923fbfe24a0dfb
Source dataset
uspto-grants-2011_02
Patent number
US07884202B2

Reaction notes

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