Reaction #710485

Reaction equation

hydroxylamine hydrochloride

triethylamine

N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide

hydrochloric acid

→

N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-hydroxyacetimidamide

Yield 63.0%

Solvents

ethanol

ethyl acetate

Conditions

Workup

1. 1
   workup.ADDITIONwere added
2. 2
   Otherliquid separation
3. 3
   Washthe organic layer was washed with water
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe organic layer was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
7. 7
   Otherto obtain the subject material
8. 8
   OtherAmount obtained 625 mg (yield 63%)

Procedure

25 ml of ethanol was added to 1.00 g (3.00 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (1-20) 1 synthesized by the method in Synthetic Example 4, 1.04 g (15.0 mmol) of hydroxylamine hydrochloride and 2.00 ml (1.50 g, 15.0 mmol) of triethylamine were added thereto in sequence, and the resulting mixture was stirred at 50° C. for 21.5 hours. After the reaction was completed, ethyl acetate and 1% hydrochloric acid were added to the reaction solution to perform liquid separation, and the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The organic layer was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the subject material. Amount obtained 625 mg (yield 63%).

Source