Hydrogen Peroxide → HCID 13025710, compound

HRID 260601Notes

Reaction equation

HRID 260601 reaction equation
[OH:1]O.[OH-].[Na+].[CH2:5]([N:12]([CH2:20][CH2:21][CH2:22][C:23]#[N:24])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH2:13]([N:12]([CH2:20][CH2:21][CH2:22][C:23]([NH2:24])=[O:1])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 2802904HCID 2802904, compound

Product 1

HCID 13025710HCID 13025710, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Hydrogen peroxide (30% w/v; 5.6 ml), tetra-n-butylammonium hydrogensulphate (1.70 g) and 5N aqueous sodium hydroxide (4 ml) were added to a stirred solution of 4-(N,N-dibenzylamino)butyronitrile (2.64 g) in dichloromethane (10 ml) with water cooling. The mixture was stirred vigorously at room temperature for 17 hours and dichloromethane (100 ml) was added. The layers were separated and the organic phase was washed with saturated aqueous sodium chloride (10 ml), dried (Na2SO4) and concentrated in vacuo to give a viscous oil (4.12 g). The product was chromatographed on silica with eluant 20% ethyl acetate/toluene→ethyl acetate and recrystallised from cyclohexane to give the title compound (1.86 g, 66%), m.p. 76°-77° C.

Workup

  1. customThe layers were separated
  2. washthe organic phase was washed with saturated aqueous sodium chloride (10 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-510bc82bd18044fd930e7ba1b9f35dcf
Source dataset
uspto-grants-1996_06
Patent number
US05527955

Reaction notes

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