Hydrogen Peroxide → Trifluoromethyluracil

HRID 1012874Notes

Reaction equation

HRID 1012874 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 0.19%

Reagents, catalysts & solvents 1

HCID 24393Ferrous SulfateCatalyst

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 trifluoromethyl iodide. The following materials were added thereinto: 2.5 ml of dibutyl sulfoxide, 0.027 ml of concentrated sulfuric acid, 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: 0.19%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard.

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-3649b394980c49439b7f43c016181775
Source dataset
uspto-grants-2011_07
Patent number
US07981318B2

Reaction notes

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