HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylamine → 5-bromo-N,N-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | 5-Bromo-2,3-dihydro-1-benzofuran-2-carboxylic acid | HCID 18624243 | — |
| Product | 5-bromo-N,N-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide | HCID 86722798 | 87% |
Reaction Steps
A mixture of 5-bromo-2,3-dihydro-1-benzofuran-2-carboxylic acid (0.243 g, 1.00 mmol) (ParkWay, Cat. No. YB-162), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.464 g, 1.05 mmol) and 2.0 M dimethylamine in tetrahydrofuran (THF) (2.00 mL, 4.00 mmol) was stirred at r.t. for 2 h. The volatiles were removed under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (gradient: 0-50%) to afford the desired product (0.235 g, 87%). LCMS (M+H)+=270.0/272.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09266892B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-9aae343104a34c03ae6c5224a42417c0 |
| Source note | uspto-grants-2016_02 |