Hydrogen Peroxide → HCID 15289123, compound

HRID 1603698Notes

Reaction equation

HRID 1603698 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-2bb7dd36ee484442bc04fb674d807f21
Source dataset
uspto-grants-1999_11
Patent number
US05990122

Reaction notes

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