Formamide → 4-(4-Bromophenyl)thiazole

To a stirred solution of phosphorus pentasulfide (24.5 g, 55 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 2,4′-dibromoacetophenone (15 g, 54 mmol) in dioxane (100 ml) was added the thioformamide solution, and the mixture was heated at reflux temperature for 6 hours. The reaction mixture was cooled down to room temperature, and made basic by addition of 2N NaOH aqueous solution. The whole was extracted with diethyl ether. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with CH2Cl2 to give title compound (12.3 g, 95% 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 6 hours
6. temperatureThe reaction mixture was cooled down to room temperature
7. extractionThe whole was extracted with diethyl ether
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 CH2Cl2

ORD record

ord-d74b04dade6440be9feab2d6f247d766

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608095B2