Hydrogen Peroxide → Trifluoromethyluracil

HRID 1012873Notes

Reaction equation

HRID 1012873 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>S([O-])([O-])(=O)=O.[Fe+2].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 90%

Reagents, catalysts & solvents 2

HCID 24393Ferrous SulfateCatalystHCID 679Dimethyl SulfoxideSolvent2×

Procedure

0.055 g (0.5 mmol) of uracil was weighed and placed in a two-neck flask and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 1.0 ml of a 1 N dimethyl sulfoxide solution of sulfuric acid, 0.5 ml of a 2.1 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.1 ml of a 30% hydrogen peroxide aqueous solution and 0.15 ml of a 1.0 mol/l aqueous solution of iron(II) sulfate, and the mixture was stirred for 20 minutes. During the stirring, the temperature of the reaction system rose up in the range of from 40° C. to 50° C. Thereafter, the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (19F-NMR yield: 90%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 5-trifluoromethyluracil was obtained as a white solid (0.16 g, yield: 87%) in the same manner as in Example 1.

Workup

  1. customplaced in a two-neck flask
  2. additionThe following materials were added
  3. customrose up in the range of from 40° C. to 50° C

Sources & evidence

ORD record
ord-7cc247df618a4996a423cc07f3ef7731
Source dataset
uspto-grants-2011_07
Patent number
US07981318B2

Reaction notes

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