Diethyl Ether → HCID 90410781, compound

Temperature

-5 °C

To a suspension of 1-(4-chlorophenyl)hydrazine as the hydrochloride salt (89.5 mg, 0.5 mmol) in Et2O (4 mL) was added a 2 N solution of LiOH (1 mL), and the resulting mixture was stirred for 15 minutes. After the system became homogeneous, the organic layer was separated and dried over Na2SO4. The resulting ethereal solution of carbohydrazide as a free base was cooled to −5° C., and then a solution of furan-2-carbonyl chloride (65 mg, 0.5 mmol) in 5 mL of THF was added dropwise to the resulting mixture. After stirring at 0° C. for 30 minutes, the reaction mixture was diluted with water (50 mL) and extracted with EtOAc (50 mL). The organic layer was then separated, washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (5-50% EtOAc in hexane) to provide 100 mg (0.382 mmol, yield 76.3%) of 3-(4-chloro-phenyl)-5-furan-2-yl-3H-[1,3,4]oxadiazol-2-one with an HPLC purity of 99.9%. LC-MS [M+H] 263.7 C12H7ClN2O3+H, expected 263.01). The 1H-NMR spectrum was in accordance with the chemical structure.

1. customthe organic layer was separated
2. dry with materialdried over Na2SO4
3. stirringAfter stirring at 0° C. for 30 minutes
4. extractionextracted with EtOAc (50 mL)
5. customThe organic layer was then separated
6. washwashed with brine
7. dry with materialdried over Na2SO4
8. customevaporated in vacuo
9. customThe residue was purified by flash chromatography on silica gel (5-50% EtOAc in hexane)

ORD record

ord-ede0606193e94595b6890a4fc6c24ea7

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09051309B2