Methanol → HCID 86739159, compound

Participants

Reaction Steps

A mixture of 3.0 gm. (0.031 mole) of N,O-dimethylhydroxylamine hydrochloride and 60 ml. of methanol was cooled in ice bath; then 6.3 gm. (0.062 mole) of triethylamine was stirred in. A solution of 4.1 gm. (0.015 mole) of 2,6-dichlorobenzylideneaminooxyacetyl chloride in toluene was added dropwise and with cooling and stirring. After one hour more at ice-bath temperature the reaction mixture was allowed to stand overnight at room temperature; then evaporate to dryness under reduced pressure. The residue was ground under water, separated, extracted with methylene chloride and the extract was treated with decolorizing carbon, then filtered. The filtrate, evaporated to dryness under reduced pressure, gave 3.1 gm. (69.1%) of a solid melting at 62°-72° C. The melt was turbid, however, and the crude product was extracted with hot n-heptane. The hot extract was passed through a Florisil* column; evaporation of the solvent left product melting at 76°-78° C. (clear).

Provenance & Evidence