Dimethylamine → HCID 13629431, compound

254 mg of 4-chloro-2-chlorocarbonyl-5-chloromethyl-4-isoxazolin-3-one were dissolved in 5 ml of benzene, and then a solution of 48 mg of dimethylamine and 107 mg of triethylamine in 2 ml of benzene were added, with stirring, at room temperature. The mixture was stirred for a further 10 minutes, after which it was washed, in turn, with 2 ml of 0.1N sulphuric acid and water (twice, 5 ml each time). The organic phase was dried over anhydrous sodium sulphate and the solvent was distilled off. The residue was purified by column chromatography through silica gel eluted with a 20:1 by volume mixture of benzene and acetone. The solvent was distilled from the eluate and the residue was recrystallized from diisopropyl ether, to give 159 mg (yield 62.8%) of the title compound in the form of crystals, melting at 107°-108° C.

1. stirringThe mixture was stirred for a further 10 minutes
2. washafter which it was washed, in turn, with 2 ml of 0.1N sulphuric acid and water (twice, 5 ml each time)
3. dry with materialThe organic phase was dried over anhydrous sodium sulphate
4. distillationthe solvent was distilled off
5. customThe residue was purified by column chromatography through silica gel
6. washeluted with a 20:1 by volume mixture of benzene and acetone
7. distillationThe solvent was distilled from the eluate
8. customthe residue was recrystallized from diisopropyl ether

ORD record

ord-f16915f40a0f4606a50c2f5ebfba39cb

Source dataset

uspto-grants-1986_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04579860