HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilyl cyanide → (8-ethoxy-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilyl cyanide | HCID 82115 | — |
| Reactant | Ytterbium triflate | HCID 2733225 | — |
| Reactant | 4-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline | HCID 18188176 | — |
| Reactant | 8-ethyl-4H-benzo[1,3]dioxine-6-carbaldehyde | HCID 59517295 | — |
| Reactant | 2-{3-[(4-carbamimidoylphenylamino)-(2-fluoro-4,5-dimethoxyphenyl)methyl]5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}benzoic Acid Trifluoroacetate | HCID 136337083 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (8-ethoxy-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile | HCID 67096857 | — |
Reaction Steps
To a solution of 230 mg of Yb(OTf)3 in 20 ml of dichloromethane there were added 650 mg of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 773 mg of 8-ethyl-4H-benzo[1,3]dioxine-6-carbaldehyde, 1g of MS3A and 0.8 ml of trimethylsilyl cyanide under a nitrogen atmosphere, and the mixture was stirred overnight at room temperature. The reaction mixture was filtered through celite, and the celite was washed with 100 ml of ethyl acetate. The organic layer was concentrated under reduced pressure to give (8-ethoxy-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile (crude product).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07928228B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-d578f82abb86488794ad4376fa539596 |
| Source note | uspto-grants-2011_04 |