tert-Butyl hydroperoxide → HCID 19768379, compound

HRID 1590953Notes

Reaction equation

HRID 1590953 reaction equation
[CH3:1][C:2]1([CH3:51])[CH2:7][CH:6]([N:8]([CH2:45][CH2:46][CH2:47][CH3:48])[C:9]2[N:14]=[C:13]([N:15]([CH2:26][CH2:27][CH2:28][CH3:29])[CH:16]3[CH2:21][C:20]([CH3:23])([CH3:22])[NH:19][C:18]([CH3:25])([CH3:24])[CH2:17]3)[N:12]=[C:11]([N:30]([CH2:41][CH2:42][CH2:43][CH3:44])[CH:31]3[CH2:36][C:35]([CH3:38])([CH3:37])[NH:34][C:33]([CH3:40])([CH3:39])[CH2:32]3)[N:10]=2)[CH2:5][C:4]([CH3:50])([CH3:49])[NH:3]1.[C:52]([O:56]O)([CH3:55])([CH3:54])C>[Mo](=O)(=O)=O.C1CCCCC1>[CH:52]1([O:56][N:34]2[C:35]([CH3:38])([CH3:37])[CH2:36][CH:31]([N:30]([CH2:41][CH2:42][CH2:43][CH3:44])[C:11]3[N:10]=[C:9]([N:8]([CH2:45][CH2:46][CH2:47][CH3:48])[CH:6]4[CH2:5][C:4]([CH3:49])([CH3:50])[N:3]([O:56][CH:52]5[CH2:55][CH2:49][CH2:4][CH2:5][CH2:54]5)[C:2]([CH3:1])([CH3:51])[CH2:7]4)[N:14]=[C:13]([N:15]([CH2:26][CH2:27][CH2:28][CH3:29])[CH:16]4[CH2:21][C:20]([CH3:22])([CH3:23])[N:19]([O:56][CH:52]5[CH2:55][CH2:21][CH2:16][CH2:17][CH2:54]5)[C:18]([CH3:24])([CH3:25])[CH2:17]4)[N:12]=3)[CH2:32][C:33]2([CH3:40])[CH3:39])[CH2:55][CH2:7][CH2:2][CH2:1][CH2:54]1

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 1562391,3,5-Triazine-2,4,6-triamine, N,N',N''-tributyl-N,N',N''-tris(2,2,6,6-tetramethyl-4-piperidinyl)-

Product 1

HCID 19768379HCID 19768379, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 14802Molybdenum trioxideCatalystHCID 8078CyclohexaneSolvent2×

Conditions

Temperature
150 °C

Procedure

To a refluxing mixture of 13.5 g (19.0 mmol) of 2,4,6-tris[N-(2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazine, 0.2 g of molybdenum trioxide, and 175 ml of cyclohexane are added 36.6 g (284 mmol) of 70% aqueous t-butyl hydroperoxide over a 10 minute interval. The red reaction mixture is heated at reflux for one hour and then transferred to a Fischer-Porter pressure bottle using 25 ml of fresh cyclohexane. The reaction mixture is then heated for 3 hours at 150° C. to discharge the red color. Solids are removed by filtration and the filtrate is concentrated to a residue which is purified by flash chromatography on silica gel (19:1 heptane:ethyl acetate). The product is crystallized from isopropyl alcohol to afford 7.6 g (40% yield) of a white powder, m.p. 189°-94° C.

Workup

  1. customThe red reaction mixture
  2. temperatureis heated
  3. temperatureat reflux for one hour
  4. customSolids are removed by filtration
  5. concentrationthe filtrate is concentrated to a residue which
  6. customis purified by flash chromatography on silica gel (19:1 heptane:ethyl acetate)
  7. customThe product is crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-46c60df4bb4d495dbf794664fb87c6f9
Source dataset
uspto-grants-1993_04
Patent number
US05204473

Reaction notes

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