HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-{[Phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | N,3-diphenylprop-2-ynamide | HCID 305965 | — |
| Reactant | Methyl 3-(bromomethyl)benzoate | HCID 517981 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-{[Phenyl-(3-phenyl propynoyl)-amino]-methyl}-benzoic acid methyl ester | HCID 67036155 | 65% |
Reaction Steps
3-Phenyl-propynoic acid phenylamide (951.4 mg, 4.3 mmol), 3-bromomethyl-benzoic acid methyl ester (1.2 g, 5.16 mmol) and Cs2CO3 (2.1 g, 6.45 mmol) were dissolved in DMF (20 ml). The mixture was stirred at room temperature for 16 h. The mixture was poured into water and extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification was by flash column chromatography on silica gel, eluting with hexanes-EtOAc (6:1 and then 4:1) afforded 3-{[phenyl-(3-phenyl-propynoyl)-amino]-methyl}-benzoic acid methyl ester 1.03 g (65%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08778973B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-a5588d5168174bca8ad2267fda08428c |
| Source note | uspto-grants-2014_07 |