HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-(Dimethylamino)ethanol → HCID 57968934, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-(Dimethylamino)ethanol | HCID 7902 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | Benzoic acid, 4-[(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-5-yl)oxy]- | HCID 25010450 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57968934 | HCID 57968934 | 58.6% |
Reaction Steps
To a clear solution of 4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-benzoic acid ((C38), 0.5 g, 1.75 mmol) in DMF (20 mL) were added N,N-dimethylamino ethanol (0.37 mL, 3.7 mmol) and EDCI (0.71 g, 3.7 mmol). The reaction was stirred at room temperature overnight. Then DMF was evaporated under vacuum. The residue was purified over sililca gel, eluting with 5% MeOH/DCM, to afford the 0.35 g of the title compound in 56% yield. 1H NMR 400 MHz (DMSO-d6) δ: 7.97 (d, J=8.9 Hz, 2H), 7.76 (d, J=7.8 Hz, 1H), 7.15-7.07 (m, 4H), 4.95 (s, 2H), 4.33 (t, J=5.5 Hz, 2H), 2.58 (t, J=5.9 Hz, 2H), 2.20 (s, 6H); MS (ES) m/z: 342 (M+H)+; HPLC purity: 91.90% (220 nm), 94.99% (254 nm).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09416146B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-547768c51498439b925fe36001b81b27 |
| Source note | uspto-grants-2016_08 |