Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanethiol | HCID 6343 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate | HCID 21883602 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69517958 | HCID 69517958 | 43% |
Reaction Steps
A mixture of ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate (Step2) (0.5 g, 1.54 mmole) and ethanethiol (0.1 g, 1.54 mmole) was dissolved in anhydrous DMF (5 mL), warmed to 90° C. and treated with K2CO3 (0.25 g, 1.84 mmole). The solution was maintained at 90° C. for 48 hrs, cooled to room temperature, filtered through celite and condensed to a viscous oil. The oil was purified by flash chromatography (silica gel) with 10-40% ethyl acetate in hexane to give light yellow solid (0.24 g, 43%): GCMS 366.00 (M+). 1H NMR (CDCl3/400 MHz) 7.60 (s, 1H), 7.27 (s, 1H), 6.77 (s, 1H), 5.67 (q, 1H, J=7.0 Hz), 4.29 (m, 2H), 2.96 (m, 2H), 1.40 (m, 3H), 1.35 (m, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07259266B2 |
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| Source dataset | uspto-grants-2007_08 |
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| ORD ID | ord-1ce93ce556644ef9ace2e069688950ea |
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| Source note | uspto-grants-2007_08 |
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