Hydrogen Peroxide → HCID 14627778, compound

HRID 260602Notes

Reaction equation

HRID 260602 reaction equation
[OH:1]O.[OH-].[Na+].[CH3:5][C:6]1[CH:26]=[CH:25][C:9]([CH2:10][N:11]([CH2:20][CH2:21][CH2:22][C:23]#[N:24])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:11]([CH2:20][CH2:21][CH2:22][C:23]([NH2:24])=[O:1])[CH2:10][C:9]2[CH:8]=[CH:7][C:6]([CH3:5])=[CH:26][CH:25]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 22401909HCID 22401909, compound

Product 1

HCID 14627778HCID 14627778, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Hydrogen peroxide (30% w/v; 5.67 ml), tetra-n-butylammonium hydrogensulphate (1.70 g) and 5N aqueous sodium hydroxide (4 ml) were added successively to a stirred solution of 4-(N,N-bis-(4-methylbenzyl)amino]butyronitrile (2.93 g) in dichloromethane (10 ml), with water cooling. The mixture was stirred vigorously at room temperature for 16 hours then dichloromethane (100 ml) was added. The layers were separated and the organic phase was washed with saturated aqueous sodium chloride (1×10 ml), dried (Na2SO4) and concentrated in vacuo to give a viscous oil (4.61 g). The product was chromatographed on silica with eluant 20% ethyl acetate/toluene→ethyl acetate and triturated with cyclohexane to give the title compound (1.77 g), m.p. 85°-86° C.

Workup

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

Sources & evidence

ORD record
ord-599fd08cbc3c47aea2d40108fdb3730d
Source dataset
uspto-grants-1996_06
Patent number
US05527955

Reaction notes

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