Dimethylformamide → HCID 19080746, compound

Participants

Reaction Steps

Dimethylformamide (13.36 g 182.7 mmol) was cooled to about 0° C. and 60.69 g (395.8 mmol) of phosphoryl chloride was added dropwise with stirring to form a pink slurry. This was allowed to warm to ambient temperature and then 32.92 g (182.7 mmol) of 1-ethyl-5-hydroxy-3-(trifluoromethyl)pyrazole was added dropwise with stirring to it. There appeared to be an endotherm and the mixture became dark brown to black. The mixture was then heated at reflux (108° C.) overnight and, after cooling, was poured into an ice-water mixture with stirring. A precipitate formed and then dissolved. The solution was extracted with dichloromethane (3×150 mL) and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound as a dark brown to black oil.

Provenance & Evidence