Hydrogen Peroxide → 8-Trifluoromethylcaffeine

HRID 1363459Notes

Reaction equation

HRID 1363459 reaction equation
[N:1]1([C:13](=[O:14])[C:12]2[N:10]([CH3:11])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].S(=O)(=O)(O)O.[F:20][C:21](I)([F:23])[F:22].OO>[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[F:20][C:21]([F:23])([F:22])[C:9]1[N:10]([CH3:11])[C:12]2[C:13](=[O:14])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=2[N:8]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 2519CaffeineHCID 16843Trifluoroiodomethane

Product 1

HCID 443226878-TrifluoromethylcaffeineYield 17%

Reagents, catalysts & solvents 3

HCID 7611Bis(eta-cyclopentadienyl) ironCatalystHCID 24393Ferrous SulfateCatalystHCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
45 °C

Procedure

0.19 g (1.0 mmol) of caffeine and 0.056 g (0.3 mmol) of ferrocene were 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: 2.0 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 of 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 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-trifluoromethylcaffeine (19F-NMR yield: 17%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard.

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-81ead22be46f4dc195d7ab006e9b2a41
Source dataset
uspto-grants-2011_02
Patent number
US07884202B2

Reaction notes

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