Thionyl Chloride → HCID 23364532, compound

Participants

Reaction Steps

A solution of 5.81 g (18.4 mmol) of N-(2-hydroxy- 1,1-dimethylethyl)-2, 4,5-trifluoro-3-(trifluoromethyl)benzamide in 100 mL of chloroform at 0° C. was treated dropwise with 5 mL of thionyl chloride. The mixture was allowed to warm to room temperature overnight. The solution was concentrated to a yellow oil which was dissolved in 20 mL of DMF and treated with 0.8 g (21.6 mmol) of 60% sodium hydride. This reaction mixture was stirred at room temperature for 18 hours, then poured into 50 mL of dilute NaHCO3. The solution was extracted with ethyl acetate; the organic phase was washed with water and dried over magnesium sulfate. Concentration in vacuo gave an orange oil which was chromatographed on silica, eluting with 2% methanol in chloroform, to give 2.62 g of a yellow oil.

Provenance & Evidence