Carbon Disulfide → HCID 178527940, compound

To a solution of 1-benzofuran-5-carbohydrazide (1.50 g, 8.51 mmol) in ethanol (60 mL) were added potassium hydroxide (0.72 g, 12.8 mmol) and carbon disulfide (15.3 mL, 25.5 mmol), and the resulting mixture was stirred at room temperature for 5 hr. The reaction mixture was concentrated under reduced pressure, a mixture of the residue and N,N-dimethylformamide (30 mL) was tightly sealed in a vial, and the microwave was irradiated at 150° C. for 1 min. After cooling, the reaction mixture was acidified with 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane/ethyl acetate to give the title compound (0.66 g, yield 36%) as colorless crystals.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additiona mixture of the residue and N,N-dimethylformamide (30 mL)
3. customwas tightly sealed in a vial, and the microwave
4. customwas irradiated at 150° C. for 1 min
5. temperatureAfter cooling
6. extractionthe mixture was extracted with ethyl acetate
7. washThe organic layer was washed with saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was recrystallized from hexane/ethyl acetate

ORD record

ord-b92e4429247045c6bb8017f35dc52523

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492378B2