Dimethyl Sulfoxide → HCID 53843285, compound

Participants

Reaction Steps

A 50 mL 3-neck round bottom flask equipped with a magnetic stirring bar and N2 inlet was charged with (0.55 g, 0.0024 mol) 2-hydroxymethyl-α-methyoxyimino-N-methyl-benzeneacetamide and 10 mL anhydrous THF. To the reaction was added (0.14 g, 0.003mol) 60% NaH with stirring under nitrogen for 20 minutes. To the reaction was then added 3-chloro-6-methylsulphonylpicolinic acid: t-butyl ester (0.900 g, 0.003 mol) dissolved in 8 mL anhydrous THF, then 2 mL DMSO and stirring for three hours under nitrogen at room temperature. The mixture was then diluted with 20 mL ethyl acetate and 50 mL DI water and extracted four times with 20 mL portions of ethyl acetate. The combined organic extracts were washed three times with 50 mL portions DI water and twice with 25 mL portions brine to give the resulting product, α-(methoxyimino)-N-methyl-2-[[[5-chloro-6-(t-butoxycarbonyl)-2-pyridinyl]oxy]methyl]-benzeneacetamide, as an off-white oily solid after chromatography. M.P. 103-108° C.

Provenance & Evidence