HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 9-Bromo-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Hydrazinecarboxaldehyde | HCID 12229 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | Ethyl (4-bromo-2-cyanophenyl)carbamate | HCID 18367857 | — |
| Product | 9-Bromo-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one | HCID 135766855 | 81% |
Reaction Conditions
| Temperature | 160 °C |
|---|
Reaction Steps
To a solution of (4-bromo-2-cyano-phenyl)-carbamic acid ethyl ester (40.4 g, 150 mmol) in NMP (170 mL) was added formylhydrazine (10.0 g, 150 mmol). The resulting mixture was stirred for 1.5 h at 160° C. under a gentle nitrogen sweep. It was cooled to below 100° C. and water (340 mL) was added slowly. The resulting slurry was cooled to 25° C. and stirred for 15 min. The solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (32.4 g, 81%) as a light yellow solid. MS: m/e 264.9/267.0 [M+H+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07507728B2 |
| Source dataset | uspto-grants-2009_03 |
| ORD ID | ord-271bca5206bf4b1ca62ec2973902481e |
| Source note | uspto-grants-2009_03 |