Hydrogen Peroxide → HCID 15289123, compound

HRID 1451718Notes

Reaction equation

HRID 1451718 reaction equation
[CH2:1]([N:8]1[C:16](=[O:17])[CH:15]2[CH:10]([C:11]3([C:20]#[N:21])[CH2:19][CH2:18][CH:14]2[CH:13]=[CH:12]3)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:23].[Na+].OO>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([N:8]1[C:16](=[O:17])[CH:15]2[CH:10]([C:11]3([C:20]([NH2:21])=[O:23])[CH2:19][CH2:18][CH:14]2[CH:13]=[CH:12]3)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 15289120HCID 15289120, compound

Product 1

HCID 15289123HCID 15289123, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

14.5 g (50 mmol) of 4-benzyl-1-cyano-4-azatricyclo[5.2.2.02,6 ]undec-8-ene-3,5-dione are dissolved in 25 ml of methylene chloride, 2.5 g of tetrabutylammonium hydrogen sulphate and 17.5 ml of 20% strength sodium hydroxide solution are added, and 24 ml of 30% strength H2O2 are added dropwise at 0° C. The mixture is stirred at 0° C. for 30 minutes and then overnight at room temperature and diluted with methylene chloride, and the organic phase is separated off and washed with sodium chloride solution. It is dried over MgSO4 and concentrated and the crystalline product is boiled up with xylene, any unreacted starting material dissolving. The product is filtered off hot with suction and dried in air.

Workup

  1. customthe organic phase is separated off
  2. washwashed with sodium chloride solution
  3. dry with materialIt is dried over MgSO4
  4. concentrationconcentrated
  5. dissolutiondissolving
  6. filtrationThe product is filtered off hot with suction
  7. customdried in air

Sources & evidence

ORD record
ord-2809b25a73a94e269d92a35298fcf57f
Source dataset
uspto-grants-1997_02
Patent number
US05605910

Reaction notes

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