Hydrogen Peroxide → HCID 135709864, compound

HRID 1012876Notes

Reaction equation

HRID 1012876 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 43%

Reagents, catalysts & solvents 2

HCID 24393Ferrous SulfateCatalystHCID 679Dimethyl SulfoxideSolvent3×

Procedure

0.10 g (0.67 mmol) of guanine 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: 130 ml of dimethyl sulfoxide, 1.3 ml of a 1 N dimethyl sulfoxide solution of sulfuric acid, 0.7 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.15 ml of a 30% hydrogen peroxide aqueous solution and 0.2 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 8-trifluoromethylguanine (19F-NMR yield: 43%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. The subsequent procedure was conducted in the same manner as in Example 1 and 8-trifluoromethylguanine was obtained as a white solid (0.018 g, yield: 8%).

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-e85c1429cc4b4adb9de2cad34c8e56c9
Source dataset
uspto-grants-2011_07
Patent number
US07981318B2

Reaction notes

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