Hydrogen Peroxide → 1,3-dimethyl-5-trifluoromethyluracil

HRID 1363440Notes

Reaction equation

HRID 1363440 reaction equation
[CH3:1][N:2]1[CH:9]=[CH:8][C:6](=[O:7])[N:5]([CH3:10])[C:3]1=[O:4].S(=O)(=O)(O)O.[F:16][C:17](I)([F:19])[F:18].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[CH3:1][N:2]1[CH:9]=[C:8]([C:17]([F:19])([F:18])[F:16])[C:6](=[O:7])[N:5]([CH3:10])[C:3]1=[O:4]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 16843TrifluoroiodomethaneHCID 701221,3-Dimethyluracil

Product 1

HCID 113332461,3-dimethyl-5-trifluoromethyluracilYield 78%

Reagents, catalysts & solvents 2

HCID 24393Ferrous SulfateCatalystHCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
45 °C

Procedure

0.14 g (1.0 mmol) of 1,3-dimethyluracil 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 of sulfuric acid, 1.0 ml of a 3.0 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 1,3-dimethyl-5-trifluoromethyluracil (19F-NMR yield: 78%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 1,3-Dimethyl-5-trifluoromethyluracil was obtained as a white solid (0.12 g, yield: 44%) 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-aac64d3bf82c4a848ffa79fc2aae4e62
Source dataset
uspto-grants-2011_02
Patent number
US07884202B2

Reaction notes

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