HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Ethyl 3-[(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | 4-Bromo-3-methoxyaniline | HCID 7018254 | — |
| Reactant | Ethyl 3-(methylamino)-3-phenylacrylate | HCID 58005139 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Ethyl 3-[(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylate | HCID 58005168 | 94% |
Reaction Steps
PPTS (38.3 g, 152 mmol) was added to a solution of the product from Step 1 (31.3 g, 152 mmol) and 4-bromo-3-methoxyaniline (28 g, 139 mmol) in DCM (700 mL). The mixture was heated to reflux and stirred for 20 h. The mixture was cooled, and the solids were removed by filtration and washed with DCM. The filtrate was concentrated and purified on silica gel (gradient elution 10% to 50% DCM in hexanes) to give the title compound (49 g, 94% yield). LRMS (M+H)+ Calcd.: 376.0; found 376.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08591878B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-119390963e3a4e00bf6763ce47cc9b00 |
| Source note | uspto-grants-2013_11 |