Carbon Disulfide → 2-(2,3-Dihydro-1-benzofuran-5-yl)-5-[(3-fluoro-4-methoxybenzyl)thio]-1,3,4-oxadiazole

To a solution of 2,3-dihydro-1-benzofuran-5-carbohydrazide (356 mg, 2.00 mmol) and potassium hydroxide (85%, 198 mg, 3.00 mmol) in ethanol (15 mL) was added carbon disulfide (0.180 mL, 3.00 mmol), and the resulting mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, a mixture of the obtained residue and N,N-dimethylformamide (10 mL) was tightly sealed in a vial, and the microwave was irradiated at 150° C. for 30 sec. After cooling to room temperature, 3-fluoro-4-methoxybenzyl chloride (698 mg, 4.00 mmol) was added, and the resulting mixture was stirred for 2 hr. The reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from hexane/ethyl acetate to give the title compound (478 mg, yield 67%) as colorless crystals.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additiona mixture of the obtained residue and N,N-dimethylformamide (10 mL)
3. customwas tightly sealed in a vial, and the microwave
4. customwas irradiated at 150° C. for 30 sec
5. temperatureAfter cooling to room temperature
6. stirringthe resulting mixture was stirred for 2 hr
7. washwashed twice with water and once with saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was crystallized from hexane/ethyl acetate

ORD record

ord-7ecb29a39cb84233a9a132e3035b270c

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492378B2