Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Benzenamine, 3,5-bis(trifluoromethyl)- | HCID 9480 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 5-(4-Chlorophenyl)-2-(trifluoromethyl)furan-3-carbonyl chloride | HCID 2736641 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86683824 | HCID 86683824 | 63.1% |
Reaction Steps
5-(4-Chloro-phenyl)-2-trifluoromethyl-furan-3-carbonyl chloride (0.050 g) was added to a solution of 3,5-bis-trifluoromethyl-phenylamine (0.034 g) and N,N-diisopropylethylamine (0.026 mL) in dichloromethane (5 mL). After stirring at room temperature for 1 day, the reaction underwent an aqueous acidic (dilute HCl, 2×5 mL) and basic (dilute NaHCO3, 2×5 mL) workup followed by washing with brine (saturated NaCl, 2×5 mL), drying over MgSO4, and concentration. The crude compound was purified by column chromatography eluting with ethyl acetate/hexanes (4:1) to afford the title compound (0.047 g, 58% yield). 1H NMR (CDCl3) δ 8.12 (s, 2H), 7.83 (bs, 1H), 7.70 (s, 1H), 7.68 (d, 2H, J=0.017 Hz), 7.47 (d, 2H, J=0.017 Hz), 7.03 (s, 1H). ES-MS negative Q1 (m/z) 501.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08722731B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-9cf32a34252e45009728e9203fa228ef |
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| Source note | uspto-grants-2014_05 |
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