Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium benzenethiol | HCID 66586497 | — |
| Reactant | HCID 178515289 | HCID 178515289 | — |
| Reactant | HCID 178516911 | HCID 178516911 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66913662 | HCID 66913662 | 57% |
Reaction Steps
3-(phenylthio)-8-(trifluoromethyl)quinolin-4-ol: A solution of 3-bromo-8-(trifluoromethyl)quinolin-4-ol (0.240 g, 0.830 mmol), sodium thiophenol (0.293 g, 45.1 mmol), is dissolved in DMF and heated in a microwave reactor for 10 min at 120° C. After which, the reaction is poured into water and extracted with ethyl acetate. The combined extracts are washed with sat aq NaHCO3, water, brine, and dried with magnesium sulfate. The extracts are concentrated and the residue is chromatographed with 1:9 ethyl acetate:hexanes to afford the title compound as a white solid (0.151 g, 57%). mp 153-155° C.; MS (ESI) m/z 322; MS (ESI) m/z 320; HRMS: calcd for C16H10NF3OS+H, 322.05134; found (ESI, [M+H]+), 322.0486.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07576215B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-cb8b9bb1afaf4672b8e9d8e9dfa9e1f7 |
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| Source note | uspto-grants-2009_08 |
|---|