Hydrogen Peroxide → Trifluoromethyluracil

HRID 1363431Notes

Reaction equation

HRID 1363431 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[F:9][C:10](I)([F:12])[F:11].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[F:9][C:10]([F:12])([F:11])[C:7]1[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][CH:8]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 1174UracilHCID 16843Trifluoroiodomethane

Product 1

HCID 5899TrifluoromethyluracilYield 94%

Reagents, catalysts & solvents 2

HCID 24393Ferrous SulfateCatalystHCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
45 °C

Procedure

0.11 g (1.0 mmol) of uracil was 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 a 1N dimethyl sulfoxide solution, 1.0 ml of a 2.1 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.2 ml of a 30% hydrogen peroxide aqueous solution and 0.3 ml of a 1.0 mol/l aqueous solution of iron (II) sulfate. 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-trifluoromethyl uracil (19F-NMR yield: 94%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 5-Trifluoromethyluracil was obtained as a white solid (0.17 g, yield: 93%) by preparative thin-layer chromatography.

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-fa3b644fc17949c3ae789db3bc5dd669
Source dataset
uspto-grants-2011_02
Patent number
US07884202B2

Reaction notes

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