Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Urea | HCID 1176 | — |
| Reactant | Methyl 3-bromo-4-oxobutanoate | HCID 13948279 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 55263325 | HCID 55263325 | 18% |
Reaction Steps
A 250-mL round bottom flask was charged with methyl 3-bromo-4-oxobutanoate (5.00 g, 25.6 mmol) and urea (2.08 g, 34.6 mmol) in DMF (15 mL) and heated to 110° C. for 30 minutes. After this time, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was absorbed onto silica and purified by chromatography on silica using dichloromethane/(89:9:1 dichloromethane/methane/conc. NH4OH) (10:0 to 0:10) as eluent, to afford the title compound (0.72 g, 18%) as a red oil. MW=156.14. 1H NMR (DMSO-d6, 300 MHz) δ 9.54 (s, 1H), 6.48 (s, 2H), 6.45 (s, 1H), 3.64 (s, 2H), 3.62 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09221843B2 |
|---|
| Source dataset | uspto-grants-2015_12 |
|---|
| ORD ID | ord-20ade2cbdd074c969623690b928ddd77 |
|---|
| Source note | uspto-grants-2015_12 |
|---|