Hydroxyamine hydrochloride → (NE)-N-[(2-chloro-6-methylsulfanylphenyl)methylidene]hydroxylamine

6-Chloro-2-(methythio)benzaldehyde (11.6 g, 75.16 mmol), and hydroxylamine hydrochloride (5.75 g, 82.86 mmol) were combined in ethanol (100 ml). Diethylamide (11.5 ml, 82.86 mmol) was slowly added to the solution and it was allowed to stir at room temperature overnight. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate and then washed successively with water and saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield (E)-2-chloro-6-(methylthio)benzaldehyde oxime (12.37 g) as a white solid. (This method is general for other 2-(methythio)benzaldehydes). 1H NMR (300 MHz, DMSO-d6): 11.62 (s, 1H), 8.22 (s, 1H), 7.20-7.40 (m, 3H), 2.41 ppm (s, 3H). MW=202 confirmed by LC-MS, tr=3.58 min (Method B) MH+=203.

1. customAfter the completion of the reaction
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. additiondiluted with ethyl acetate
4. washwashed successively with water and saturated aqueous sodium bicarbonate solution
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-9b29f6d18c1f4deb90a61de25a5f7415

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07776847B2