Semicarbazide → HCID 136641697, compound

3-(Benzyloxy)-2,2-dimethylpropanoic acid (1.00 g, 4.80 mmol) was dissolved in DCM (10 mL) at RT. Oxalyl chloride (0.70 mL, 8.00 mmol) and DMF (0.10 mL, 1.29 mmol) were added sequentially and the reaction mixture was stirred at RT for 2 h. In a separate flask, semicarbazide hydrochloride (0.8 g, 7.24 mmol) and NaOH (0.80 g, 20.0 mmol) were dissolved in a solution of dioxane (2.0 mL) and water (10.0 mL). The solution of the acid chloride was added in one portion to the solution of the semicarbazide and the reaction mixture was stirred at RT for 12 h. 2 M NaOH (aq.) (28.0 mL, 56.0 mmol) was then added and the reaction mixture was stirred at 100° C. for 2 h, allowed to cool to RT, and neutralized by the addition of ¾ sat. NH4Cl (aq.) (75 mL). The resultant homogenous solution was sonicated for 12 h and the resultant precipitated solids were collected by filtration and dried in vacuo to afford 3-(1-(benzyloxy)-2-methylpropan-2-yl)-1H-1,2,4-triazol-5(4H)-one (0.57 g, 48.0%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.22 (s, 1H), 11.09 (s, 1H), 7.34-7.23 (m, 5H), 4.44 (s, 2H), 3.39 (s, 2H), 1.16 (s, 5H).

1. stirringthe reaction mixture was stirred at RT for 12 h
2. stirringthe reaction mixture was stirred at 100° C. for 2 h
3. temperatureto cool to RT
4. customThe resultant homogenous solution was sonicated for 12 h
5. customthe resultant precipitated solids
6. filtrationwere collected by filtration
7. customdried in vacuo

ORD record

ord-b8b710ae593e462e8327a0b6f622729f

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193719B2