Hydrogen Peroxide → HCID 57693397, compound

HRID 1363460Notes

Reaction equation

HRID 1363460 reaction equation
[NH:1]1[C:12](=[O:13])[C:11]2[N:9]([CH3:10])[CH:8]=[N:7][C:6]=2[N:4]([CH3:5])[C:2]1=[O:3].S(=O)(=O)(O)O.[F:19][C:20](I)([F:22])[F:21].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[F:19][C:20]([F:22])([F:21])[C:8]1[N:9]([CH3:10])[C:11]2[C:12](=[O:13])[NH:1][C:2](=[O:3])[N:4]([CH3:5])[C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 5429TheobromineHCID 16843Trifluoroiodomethane

Product 1

HCID 57693397HCID 57693397, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 24393Ferrous SulfateCatalystHCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
45 °C

Procedure

0.18 g (1.0 mmol) of theobromine 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: 17 ml of dimethyl sulfoxide, 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, 0.3 ml of a 1.0 mol/l aqueous solution of iron (II) sulfate and 0.2 ml of a 30% hydrogen peroxide aqueous solution. The mixture was stirred at 40 to 50° C. for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 8-trifluoromethyltheobromine (19F-NMR yield: 12%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 8-Trifluoromethyltheobromine was obtained as a white solid (0.024 g, yield: 10%) by column 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-152828d5f2744113bf3f51e5efffa7fd
Source dataset
uspto-grants-2011_02
Patent number
US07884202B2

Reaction notes

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