HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 18677024, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | P-Xylene | HCID 7809 | — |
| Reactant | Ethyl Acetoacetate | HCID 8868 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 3-Fluorobenzene-1,2-diamine | HCID 2782835 | — |
| Product | HCID 18677024 | HCID 18677024 | 8% |
Reaction Steps
A mixture of 3-fluorobenzenediamine (6.3 g, 50.0 mmol) and ethyl acetoacetate (6.50 g, 50.0 mmol) and DBU (0.76 g, 5.0 mmol) in p-xylene (50 mL) was heated to reflux for 2 h. Water formed during reaction was removed with a Dean-Stark trap. After cooling, the solvent was removed in vacuo. The residue was purified by flash chromatography (gradient, hexanes:EtOAc 4:1 to 1:1) to give 0.76 mg (8%) of 5-fluoro-1-isopropenyl-1,3-dihydro-benzoimidazol-2-one, 261 and 1.10 (11%) of 6-fluoro-1-isopropenyl-1,3-dihydro-benzoimidazol-2-one 262 as white solids.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06506738B1 |
| Source dataset | uspto-grants-2003_01 |
| ORD ID | ord-bb05a86b9f4c4232ba94bc7c835a6097 |
| Source note | uspto-grants-2003_01 |