Hydrogen Peroxide → Trifluoromethyluracil

HRID 1363434Notes

Reaction equation

HRID 1363434 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].C(S(CCCC)=O)CCC.S(=O)(=O)(O)O.OO>S([O-])([O-])(=O)=O.[Fe+2]>[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

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 1174UracilHCID 16568Dibutyl sulfoxideHCID 16843Trifluoroiodomethane

Product 1

HCID 5899TrifluoromethyluracilYield 0.2%

Reagents, catalysts & solvents 1

HCID 24393Ferrous SulfateCatalyst

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 trifluoromethyl iodide. The following materials were added thereinto: 5.0 ml of dibutyl sulfoxide, 0.053 ml of concentrated sulfuric acid, 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-trifluoromethyluracil (19F-NMR yield: 0.2%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard.

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-5cafe6227a614155ad8becbb50146225
Source dataset
uspto-grants-2011_02
Patent number
US07884202B2

Reaction notes

Loading…