Water → 1-(5,6-Dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone oxime

1-(5,6-Dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (0.3005 g; 1.062 mmoles) and hydroxylamine hydrochloride (0.2389 g, 3.438 mmoles) were suspended in pyridine (3 mL) and ethanol (3 mL), then heated to 70° C. for 3 hrs. The reaction mixture was cooled to room temperature, water was water (50 mL) and the reaction mixture was then extracted with ethyl acetate (3×40 ml). The extracts were combined then washed with water (20 mL), brine (30 mL) and dried over Na2SO4. The filtrate was concentrated in vacuo and purifed by column chromatography (SiO2; 30% ethyl acetate/CH2Cl2) to yield the title compound as an off-white solid, as a mixture of oxime E and Z isomers.

1. extractionthe reaction mixture was then extracted with ethyl acetate (3×40 ml)
2. washThe extracts were combined then washed with water (20 mL), brine (30 mL)
3. dry with materialdried over Na2SO4
4. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-e1e2ee9f151045589feae63bf3028ea7

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07566733B2