Sodium Hydroxide → N-[2-(5-bromo-3-chloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzthioamide

Participants

Reaction Conditions

Reaction Steps

To 222 mg of the N-[2-(5-bromo-3-chloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide prepared in Step 4 in Synthetic Example 20 in 5 ml of 1,4-dioxane, 200 mg of Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide) was added, and the mixture was stirred at 80° C. for 3 hours and then at room temperature for 12 hours. After completion of the reaction, the reaction mixture was mixed with 40 ml of 0.05M aqueous sodium hydroxide and extracted with a mixture of ethyl acetate-diethyl ether (2:1) (30 ml×1), the resulting organic layer was washed with 40 ml of 0.2M aqueous sodium hydroxide and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 2:8) as the eluent to obtain 133 mg of the desired product as a brown resinous substance.

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