Hydrogen Peroxide → 2,4-Bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-s-triazine

Participants

Reaction Conditions

Reaction Steps

A solution of 0.188 g (0.676 mmol) of ferrous sulfate heptahydrate and 0.25 g (2.6 mmol) of methanesulfonic acid in 2 ml of water is added to a mixture of 5.00 g (8.83 mmol) of 2-chloro-4,6-bis[N-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazine, 29 ml of acetonitrile, and 18 ml of cyclohexane. The reaction mixture is heated to 52° C. A solution of 4.87 g (72 mmol) of 50% aqueous hydrogen peroxide is added dropwise to the reaction mixture over 2.25 hours while the temperature is brought to and maintained at 62° C. After the peroxide is added, the reaction mixture is stirred at reflux for 45 minutes, then cooled prior to decomposing residual peroxide with aqueous sodium sulfite. Work-up and purification according to the procedure of Example 5 afford 3.23 g (50% yield) of the title compound, a white glass. Structure is verified by NMR and ms analysis.

Provenance & Evidence