Bromine → HCID 17863040, compound

To a solution (70 mL) of 1-(3-methylphenyl)-2-(4-pyrimidinyl)ethenol (3.0 g, 14 mmol) and sodium acetate (2.32 g, 28.26 mmol) in acetic acid was added dropwise a solution (70 mL) of bromine (0.72 mL, 14 mmol) in acetic acid at room temperature over 30 min. The mixture was stirred at room temperature for 2 hrs. Acetic acid was evaporated under reduced pressure, and aqueous sodium hydrogen carbonate solution was added to the residue. The mixture was extracted with ethyl acetate and the extract was dried and concentrated. The residue was dissolved in N,N-dimethylformamide (15 mL), and thiourea (1.1 g, 16 mmol) was added to the solution. The reaction mixture was stirred at room temperature for 14 hrs. Aqueous sodium hydrogen carbonate solution was added, and the precipitated solids were collected by filtration. The solids were washed with water, dried and subjected to recrystallization from ethyl acetate to give the title compound (3.4 g, yield 89%).

1. customAcetic acid was evaporated under reduced pressure, and aqueous sodium hydrogen carbonate solution
2. additionwas added to the residue
3. extractionThe mixture was extracted with ethyl acetate
4. customthe extract was dried
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in N,N-dimethylformamide (15 mL)
7. stirringThe reaction mixture was stirred at room temperature for 14 hrs
8. filtrationthe precipitated solids were collected by filtration
9. washThe solids were washed with water
10. customdried
11. customsubjected to recrystallization from ethyl acetate

ORD record

ord-bc549d05a45249879c530b88c7dd8e2f

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199124B2