Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 2-Thiophenecarbonyl chloride | HCID 78928 | — |
| Reactant | Benzenamine, 3-ethynyl- | HCID 104682 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 1070379 | HCID 1070379 | 85% |
Reaction Steps
A dry 25 mL flask was charged with thiophene-2-carbonyl chloride and THF (5 mL) was added. 3-Ethynyl-phenylamine (0.905 g, 3.59 mmol) was added to the THF solution of the acid chloride followed by NEt3, and the mixture was allowed to stir at 55° C. The reaction mixture was then allowed to cool to room temperature and extracted with EtOAc (˜10 mL), 1M HCl (˜10 mL), followed by brine (˜10 mL). The combined organic extracts were combined and dried over anhydrous Na2SO4(s) and the concentrated. The crude residue was purified by chromatography (silica gel, gradient elution EtOAc/Hexanes 0 to 50%). The product containing fractions were concentrated to give the title compound as a tan solid (0.33 mg, 1.45 mmol, 85%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08383825B2 |
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| Source dataset | uspto-grants-2013_02 |
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| ORD ID | ord-242f11cecf1c44939decf14b0bcebea3 |
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| Source note | uspto-grants-2013_02 |
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