Hydrogen Peroxide → Dibenzylhydroxylamine

HRID 378595Notes

Reaction equation

HRID 378595 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([O-])([O-])(=O)=[O:17].[Mg+2].OO.[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26]>CC(C)=O.C[Re](=O)(=O)=O.C(OCC)(=O)C>[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26].[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[OH:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

9

Reactant 4

HCID 784Hydrogen PeroxideHCID 971Oxalic AcidHCID 7656DibenzylamineHCID 24083Sulfuric acid magnesium salt (1:1)

Product 2

HCID 971Oxalic AcidHCID 69297DibenzylhydroxylamineYield 102.7%

Reagents, catalysts & solvents 3

HCID 178477782HCID 178477782, compoundCatalystHCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dibenzylamine (3.0 g, 0.0152 mole) was added with ethyl acetate (15 ml) and anhydrous magnesium sulfate (3 g), and the mixture was stirred under ice cooling. A solution of methyltrioxorhenium (0.0114 g, 0.0457 mmole) dissolved in 35% aqueous hydrogen peroxide (1.8 g, 0.018 mole) was added dropwise to the mixture over 1 hour so as to keep internal temperature at 5° C. to 10° C. After the reaction mixture was stirred at the same temperature for 1 hour, the magnesium sulfate was removed by filtration, and the filtrate was added with a solution of oxalic acid (1.23 g, 0.0137 mole) dissolved in acetone (7 ml). The mixture was stirred for 30 minutes under ice cooling, and the precipitated crystals were collected by filtration to obtain oxalic acid salt of N,N-dibenzylhydroxylamine (3.0 g, yield: 65.2%) having melting point of 152-153° C. Chemical structure of the product was analyzed by 1H-NMR, mass spectrometry and elemental analysis. 1H-NMR (DMSO-D6) σ (ppm) (multiplicity, integrated value): 7.45-7.12 (m, 11H), 3.85 (s, 4H). Elemental analysis, calculated for C16H17N1O5 : C, 63.36; H, 5.65; N, 4.62, found: C, 63.30; H, 5.65; N, 4.62.

Workup

  1. additionwas added dropwise to the mixture over 1 hour so as
  2. customat 5° C. to 10° C
  3. stirringAfter the reaction mixture was stirred at the same temperature for 1 hour
  4. customthe magnesium sulfate was removed by filtration
  5. stirringThe mixture was stirred for 30 minutes under ice cooling
  6. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-85c9c284e44448ccaf52ae28aa0a73b3
Source dataset
uspto-grants-2000_02
Patent number
US06031130

Reaction notes

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