Hydrogen Peroxide → HCID 19354384, compound

Participants

Reaction Steps

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).

Provenance & Evidence