HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 1-[3-Cyclopentyl-2-(4-nitro-phenyl)-propionyl]-3-methyl-urea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Methylurea | HCID 11719 | — |
| Reactant | Methanol, magnesium salt (2:1) | HCID 164537 | — |
| Reactant | 3-Cyclopentyl-2-(4-nitro-phenyl)-propionic acid ethyl ester | HCID 11471849 | — |
| Product | 1-[3-Cyclopentyl-2-(4-nitro-phenyl)-propionyl]-3-methyl-urea | HCID 12044454 | 13.2% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
A mixture of 3-cyclopentyl-2-(4-nitro-phenyl)-propionic acid ethyl ester (1.27 g, 4.36 mmol) and methyl urea (647 mg, 8.73 mmol) in a solution of magnesium methoxide in methanol (7.4 wt %, 9.36 mL, 6.54 mmol) was refluxed at 100° C. for 8.5 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 1-[3-cyclopentyl-2-(4-nitro-phenyl)-propionyl]-3-methyl-urea (183.6 mg, 13.2%) as a white solid: mp 179-183° C.; EI-HRMS m/e calcd for C16H21N3O4(M+) 319.1532, found 319.1527.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06528543B1 |
| Source dataset | uspto-grants-2003_03 |
| ORD ID | ord-05706b9ec4744fb199042f56ce6bca39 |
| Source note | uspto-grants-2003_03 |