Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Bromoethanol | HCID 10898 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 21638785 | HCID 21638785 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 22660615 | HCID 22660615 | 42.8% |
Reaction Steps
The product from Step B (1.0 g) was dissolved in CH3CN (10 mL) and treated with 2-bromoethanol (0.5 g) and then K2CO3 (0.8 g). The resulting mixture was heated at 60° C. overnight. The mixture was cooled to ambient temperature, filtered, and concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography (0-10% methanol/dichloromethane) to give the title compound (0.5 g). 1H NMR (400 MHz, CDCl3): δ 10.09 (br s, 1H), 7.61 (d, J=2.0 Hz, 1H), 7.37 (d, J=8.8 Hz, 1H), 7.23 (dd, J=2.0, 8.8 Hz, 1H), 6.69 (d, J=0.8 Hz, 1H), 3.95 (br m, 3H), 3.72-3.69 (m, 2H), 2.67-2.64 (m, 4H), 2.52 (br s, 3H). MS (electrospray): exact mass calculated for C15H18ClN3O2, 307.78; m/z found, 308.1 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06803362B2 |
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| Source dataset | uspto-grants-2004_10 |
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| ORD ID | ord-3ed1fc0c14c446faab33ca054a804788 |
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| Source note | uspto-grants-2004_10 |
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