Hydrogen Peroxide → HCID 57172614, compound

HRID 650430Notes

Reaction equation

HRID 650430 reaction equation
OO.[OH:3][N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]2[N:22]=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]3[CH2:33][C:32]([CH3:35])([CH3:34])[N:31]([OH:36])[C:30]([CH3:38])([CH3:37])[CH2:29]3)[N:20]=[C:19]([NH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH:44]3[CH2:49][C:48]([CH3:51])([CH3:50])[N:47]([OH:52])[C:46]([CH3:54])([CH3:53])[CH2:45]3)[N:18]=2)[CH2:6][C:5]1([CH3:56])[CH3:55].S([O-])([O-])=O.[Na+].[Na+].[C:63]([OH:67])([CH3:66])([CH3:65])[CH3:64]>O.C(OCC)(=O)C>[OH:67][C:63]([CH3:66])([CH3:65])[CH2:64][O:52][N:47]1[C:46]([CH3:54])([CH3:53])[CH2:45][CH:44]([CH2:43][CH2:42][CH2:41][CH2:40][NH:39][C:19]2[N:18]=[C:17]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:7]3[CH2:6][C:5]([CH3:56])([CH3:55])[N:4]([O:3][CH2:64][C:63]([CH3:66])([OH:67])[CH3:65])[C:9]([CH3:11])([CH3:10])[CH2:8]3)[N:22]=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]3[CH2:33][C:32]([CH3:34])([CH3:35])[N:31]([O:36][CH2:64][C:63]([CH3:66])([OH:67])[CH3:65])[C:30]([CH3:38])([CH3:37])[CH2:29]3)[N:20]=2)[CH2:49][C:48]1([CH3:51])[CH3:50]

Participants

7

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 69201187HCID 69201187, compound

Product 1

HCID 57172614HCID 57172614, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 40 g (0.35 mol) of 30% aqueous hydrogen peroxide is added over 1.25 hours to a mixture of 11.7 g (0.011 mol) of 2,4,6-tris[N-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl]butylamino}-s-triazine and 3.0 g (0.015 mol) of ferrous chloride tetrahydrate in 100 g of tert-butyl alcohol and 9 g of water. The reaction temperature is maintained at 60-65° C. during the peroxide addition. Two equal portions (2 g, 0.29 mol) of 50% aqueous hydrogen peroxide are added to the reaction mixture while the temperature is maintained at 60° C. for 9.5 hours. After the reaction mixture is diluted with ethyl acetate and cooled to room temperature, a solution of 100 g of 20% aqueous sodium sulfite is added. The reaction mixture is heated at 60° C. for one hour to decompose the excess peroxide. The aqueous layer is extracted with ethyl acetate, and the combined organic layers are concentrated. The crude product is purified by flash chromatography on silica gel with 2:1 (v/v) cyclohexane/ethyl acetate to afford a material which is triturated with 1:1 (v/v) cyclohexane/acetone to give 4.0 g of the title compound as a white solid, melting at 172-176° C.

Workup

  1. temperaturecooled to room temperature
  2. temperatureThe reaction mixture is heated at 60° C. for one hour
  3. extractionThe aqueous layer is extracted with ethyl acetate
  4. concentrationthe combined organic layers are concentrated
  5. customThe crude product is purified by flash chromatography on silica gel with 2:1 (v/v) cyclohexane/ethyl acetate
  6. customto afford a material which
  7. customis triturated with 1:1 (v/v) cyclohexane/acetone

Sources & evidence

ORD record
ord-92476a8a732f4c8f9710a97b4d8b25b6
Source dataset
uspto-grants-2001_08
Patent number
US06271377B1

Reaction notes

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