Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Ethyl Thioglycolate | HCID 12185 | — |
| Reactant | 3-Chloro-5-(trifluoromethyl)picolinaldehyde | HCID 22018790 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 2809345 | HCID 2809345 | — |
Reaction Steps
3-Chloro-5-(trifluoromethyl)-2-pyridinecarbaldehyde (Chemical Abstracts number 175277-50-6, purchase from Maybridge), potassium carbonate (4.95 g), and ethyl mercaptoacetate (2.52 g) were combined in N,N-dimethylformamide (25 mL) at 25° C. and stirred for 18 hours. The mixture was then heated at 50° C. for 6 hours, allowed to cool to room temperature, poured into a mixture of diethyl ether (80 mL) and dichloromethane (25 mL), and washed with aqueous sodium carbonate. The organic phase was dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was dissolved in dichloromethane and filtered to remove solids. The filtrate was concentrated and the residue purified by flash chromatography (dichloromethane) to provide the title compound. MS (DCI/NH3) m/z 276.0 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07470691B2 |
|---|
| Source dataset | uspto-grants-2008_12 |
|---|
| ORD ID | ord-9a8f803ef61b491c9eaa9b5d542a0211 |
|---|
| Source note | uspto-grants-2008_12 |
|---|