Hydrogen Peroxide → HCID 19354384, compound

HRID 378594Notes

Reaction equation

HRID 378594 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][Cl:7].S([O-])([O-])(=O)=[O:9].[Mg+2].OO.[C:16]([OH:21])(=[O:20])[C:17]([OH:19])=[O:18]>CC(C)=O.C[Re](=O)(=O)=O.C(OCC)(=O)C>[C:16]([OH:21])(=[O:20])[C:17]([OH:19])=[O:18].[Cl:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][Cl:7])[OH:9]

Participants

9

Reactant 4

HCID 784Hydrogen PeroxideHCID 971Oxalic AcidHCID 9533Bis(2-chloroethyl)amineHCID 24083Sulfuric acid magnesium salt (1:1)

Product 2

HCID 971Oxalic AcidHCID 19354384HCID 19354384, compoundYield 108%

Reagents, catalysts & solvents 3

HCID 178477782HCID 178477782, compoundCatalystHCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bis(2-chloroethyl)amine (3.0 g, 0.0211 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 (0.0104 g, 0.0417 mmole) dissolved in 35% aqueous hydrogen peroxide (2.5 g, 0.025 mole) was added dropwise to the mixture over 1 hour so as to keep internal temperature at from 5° C. to 10° C. After the reaction mixture was stirred at room temperature for 1 hour, the magnesium sulfate was removed by filtration, and the filtrate was added with a solution of oxalic acid (1.9 g, 0.0211 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-bis(2-chloroethyl)hydroxylamine (3.6 g, yield: 68.0%) having melting point of 134-135° C. Structure of the product was analyzed by 1H-NMR and mass spectrometry. 1H-NMR (DMSO-D6) σ (ppm) (multiplicity, integrated value): 8.57-7.80 (br, 1H), 5.95-4.96 (br, 1H), 3.71 (t, 4H), 2.92 (t, 4H).

Workup

  1. additionwas added dropwise to the mixture over 1 hour so as
  2. customat from 5° C. to 10° C
  3. stirringAfter the reaction mixture was stirred at room 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-ca3350bc56114e11894c728a0bea665d
Source dataset
uspto-grants-2000_02
Patent number
US06031130

Reaction notes

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