Hydrogen Peroxide → HCID 135709864, compound

HRID 1363454Notes

Reaction equation

HRID 1363454 reaction equation
[NH:1]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]=[C:2]1[NH2:3].S(=O)(=O)(O)O.[F:17][C:18](I)([F:20])[F:19].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[F:17][C:18]([F:20])([F:19])[C:7]1[NH:8][C:9]2[C:10](=[O:11])[NH:1][C:2]([NH2:3])=[N:4][C:5]=2[N:6]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 16843TrifluoroiodomethaneHCID 135398634Guanine

Product 1

HCID 135709864HCID 135709864, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 24393Ferrous SulfateCatalystHCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
45 °C

Procedure

0.15 g (1.0 mmol) of guanine was weighed and placed in a 500 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: 197 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, 0.2 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 8-trifluoromethylguanine (19F-NMR yield: 46%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 8-Trifluoromethylguanine was obtained as a white solid (0.019 g, yield: 9%) by column chromatography.

Workup

  1. customplaced in a 500 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-357a527eb0c04770af976deab50791ba
Source dataset
uspto-grants-2011_02
Patent number
US07884202B2

Reaction notes

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