Water → HCID 58734278, compound

Temperature

65 °C

After 6-trifluoromethylpyridin-3-ylamine (1.00 g, 6.02 mmol) was dissolved in 1N hydrochloric acid (15 ml) and methanol (3 ml), a water (3 ml) solution of sodium nitrite (506 mg, 7.22 mmol) was added dropwise to the resulting solution at −10° C. The reaction mixture was added dropwise to a water (15 ml) solution of potassium o-ethyl dithiocarbonate (1.93 g, 12.0 mmol) heated to 65° C. At the same temperature, the reaction mixture was stirred for 30 minutes. After the reaction mixture was cooled to room temperature, the product thus obtained was extracted with ethyl acetate. The extract was washed with brine. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=100:1 eluate was concentrated under reduced pressure to give the title compound (895 mg, 3.35 mmol, 56%) as a yellow oil.

1. temperatureAfter the reaction mixture was cooled to room temperature
2. customthe product thus obtained
3. extractionwas extracted with ethyl acetate
4. washThe extract was washed with brine
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure
8. customThe residue thus obtained
9. concentrationethyl acetate=100:1 eluate was concentrated under reduced pressure

ORD record

ord-a5f89d74079743c5a83e6ac2fbe5539c

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932271B2