Hydrochloric Acid → HCID 135519035, compound

4-Fluorobenzoyl chloride (2.50 g, 15.77 mmol) was added to a solution of semicarbazide hydrochloride (2.00 g, 17.93 mmol) and sodium bicarbonate (2.50 g, 29.8 mmol) in water (25 mL) and the mixture was stirred at RT for 2 h. The solids were collected by filtration, and washed and dried under suction to obtain a white solid. MS (ESI) m/z: 198.1 (M+H+). The solid was suspended in water (25 mL), treated with sodium hydroxide (1.50 g, 37.5 mmol) and heated at 100° C. for 5 hours. The reaction mixture was cooled in ice bath, acidified with conc. HCl and stirred for 20 min. The solids were collected by filtration. The white solid was stirred in acetonitrile filtered, washed and dried to provide 3-(4-fluorophenyl)-1H-1,2,4-triazol-5(4H)-one (1.1 g, 38.9% yield) as white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.03 (s, 1H), 11.65 (s, 1H), 7.81 (m, 2H), 7.31 (m, 2H); MS (ESI) m/z: 180.1 (M+H+).

1. filtrationThe solids were collected by filtration
2. washwashed
3. customdried under suction
4. customto obtain a white solid
5. temperatureheated at 100° C. for 5 hours
6. temperatureThe reaction mixture was cooled in ice bath
7. stirringstirred for 20 min
8. filtrationThe solids were collected by filtration
9. stirringThe white solid was stirred in acetonitrile
10. filtrationfiltered
11. washwashed
12. customdried

ORD record

ord-4dc27dedecef4dbfa23ddea1811e2dd5

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193719B2