HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-(4-chloro-phenyl)-N-methoxy-N-methyl-acrylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Propenoic acid, 3-(4-chlorophenyl)- | HCID 15371 | — |
| Reactant | O-Methylhydroxylamine hydrochloride | HCID 521874 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-(4-chloro-phenyl)-N-methoxy-N-methyl-acrylamide | HCID 73851574 | 86.2% |
Reaction Steps
A mixture of 4-chlorocinnamic acid (18.3 g), EDAC.HCl (23 g), DMAP (12.2 g), triethylamine (28 mL), and NH2OMe.HCl (12 g) in CH2Cl2 (300 mL) was stirred at room temperature for 16 h. The reaction was quenched with water, and the organic layer was washed with brine, dried over MgSO4 and filtered. The filtrated was evaporated in vacuo, and the crude product was purified by silica gel flash chromatography eluting with 33% hexanes in ethyl acetate gave the title compound (19.5 g) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07144881B2 |
| Source dataset | uspto-grants-2006_12 |
| ORD ID | ord-282eac3c6f714a0fbd60893071680579 |
| Source note | uspto-grants-2006_12 |