HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl diazoacetate → Ethyl 3-(4-chlorophenyl)-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl diazoacetate | HCID 12192 | — |
| Reactant | Maleimide, N-(p-chlorophenyl)- | HCID 15400 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | Ethyl 3-(4-chlorophenyl)-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate | HCID 3120146 | 35% |
Reaction Steps
A solution of 19.4 g (93 mmol) of 1-(4-chloro-phenyl)-pyrrole-2,5-dione in 120 ml of xylene was treated with 19.4 ml (187 mmol) of ethyldiazoacetate and refluxed during 12 hrs. Evaporation of the solvent and chromatography on silica gel with toluene and then a gradient of toluene/AcOEt from 95:5 to 90:10 gave 9.5 g(35%) of the title compound. Off white solid. MS: 294 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07501413B2 |
| Source dataset | uspto-grants-2009_03 |
| ORD ID | ord-01f24a38bb21480da8e3ab11a692e97a |
| Source note | uspto-grants-2009_03 |