Hydrochloric Acid → HCID 136197533, compound

Temperature

-10 °C

To a suspension of semicarbazide hydrochloride (5.00 g, 44.8 mmol) in DCM (100 mL) was added triethylamine (10.00 g, 99 mmol) and the mixture was stirred at −10° C. for 30 min. Cyclopropane carbonylchloride (5.00 g, 47.8 mmol) was added at the same temp and the mixture was stirred to RT over night. The solvent from the reaction mixture was completely removed and the residue stirred in MeCN (200 mL) for 1 h. The solids were collected by filtration, washed and dried. The solid was transferred to a RB flask and treated with sodium hydroxide (7.00 g, 175 mmol) and water (20 mL). The resulting reaction mixture was heated at 100° C. for 2 hours. The reaction mixture was cooled and acidified with conc. HCl. The solids were collected by filtration, washed and dried to provide 3-cyclopropyl-1H-1,2,4-triazol-5(4H)-one (1.82 g, 30.4% yield) as white solid. 1H NMR (400 MHz, DMSO-d6): δ11.03 (br s, 2H), 1.67 (m, 1H), 0.82 (m, 2H), 0.73 (m, 2H); MS (ESI) m/z: 126.1 (M+H+).

1. stirringthe mixture was stirred to RT over night
2. customThe solvent from the reaction mixture was completely removed
3. stirringthe residue stirred in MeCN (200 mL) for 1 h
4. filtrationThe solids were collected by filtration
5. washwashed
6. customdried
7. customThe resulting reaction mixture
8. temperaturewas heated at 100° C. for 2 hours
9. temperatureThe reaction mixture was cooled
10. filtrationThe solids were collected by filtration
11. washwashed
12. customdried

ORD record

ord-502cb3d89b864117b2361a7a6b596642

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193719B2