Formamide → HCID 22316642, compound

To a stirred suspension of phosphorus pentasulfide (24.5 g, 110 mmol) in dioxane (250 ml) was added formamide (28.4 g. 630 mmol), and the mixture was heated at reflux temperature for 2 hours. The reaction mixture was cooled down to room temperature, and the solution was decanted away from solids. To a stirred solution of 1-(4-acetylphenyl)-2-bromo-1-ethanone (2.0 g, 8.3 mmol) in dioxane (80 ml) was added the thioformamide solution, and the mixture was heated at reflux temperature for 13 hours. The reaction mixture was cooled down to room temperature, and made basic by addition of 0.5M NaOH aqueous solution. The whole was extracted with diethylether. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:4) to give the title compound (610 mg, 36% yield).

1. temperaturethe mixture was heated
2. temperatureat reflux temperature for 2 hours
3. customthe solution was decanted away from solids
4. temperaturethe mixture was heated
5. temperatureat reflux temperature for 13 hours
6. temperatureThe reaction mixture was cooled down to room temperature
7. extractionThe whole was extracted with diethylether
8. washThe organic layer was washed with brine
9. dry with materialdried over MgSO4
10. concentrationconcentrated in vacuo
11. customThe residue was purified by flash chromatography
12. washeluting with ethyl acetate-hexane (1:4)

ORD record

ord-460544d78d7c47dd830ec9a862aeb1e4

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06949536B2