Hydrochloric Acid → HCID 136197531, 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. Cyclopentane carbonylchloride (5.00 g, 37.7 mmol) was added at the same temp and the mixture was allowed to warm 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 treated with sodium hydroxide (7.00 g, 175 mmol) and water (20 mL). The resulting reaction mixture was heated at 100° C. for 3 h. The reaction mixture was cooled and acidified with conc. HCl. The solids were collected, washed and dried to provide 3-cyclopentyl-1H-1,2,4-triazol-5(4H)-one (2.24 g, 38.8% yield) as white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.17 (s, 1H), 11.03 (s, 1H), 2.80 (m, 1H), 1.86 (m, 2H), 1.58 (m, 6H); MS (ESI) m/z: 154.1 (M+H+).

1. temperatureto warm 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 3 h
9. temperatureThe reaction mixture was cooled
10. customThe solids were collected
11. washwashed
12. customdried

ORD record

ord-b67e784c2da34f468abd67166ff7692d

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193719B2