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

HRID 133636Notes

Reaction equation

HRID 133636 reaction equation
CS(O)(=O)=O.[Cl:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][C:22]([CH3:25])([CH3:24])[N:21]([OH:26])[C:20]([CH3:28])([CH3:27])[CH2:19]2)[N:10]=[C:9]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]2[CH2:39][C:38]([CH3:41])([CH3:40])[N:37]([OH:42])[C:36]([CH3:44])([CH3:43])[CH2:35]2)[N:8]=1.OO.S([O-])([O-])=O.[Na+].[Na+].[CH2:53]1[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1>O.C(#N)C>[Cl:6][C:7]1[N:8]=[C:9]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]2[CH2:35][C:36]([CH3:44])([CH3:43])[N:37]([O:42][CH:53]3[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]3)[C:38]([CH3:41])([CH3:40])[CH2:39]2)[N:10]=[C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]2[CH2:19][C:20]([CH3:28])([CH3:27])[N:21]([O:26][CH:53]3[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]3)[C:22]([CH3:24])([CH3:25])[CH2:23]2)[N:12]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 6395Methanesulfonic AcidHCID 8078CyclohexaneHCID 24437Sodium SulfiteHCID 570971972,4-bis[N-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-s-triazine

Product 1

HCID 225076382,4-Bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-s-triazineYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
52 °C

Procedure

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.

Workup

  1. temperaturemaintained at 62° C
  2. temperatureat reflux for 45 minutes
  3. temperaturecooled
  4. custompurification

Sources & evidence

ORD record
ord-77ddd57c52014ca99216b7034b28762d
Source dataset
uspto-grants-2008_06
Patent number
US07390904B2

Reaction notes

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