Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 3-Amino-5-fluorobenzotrifluoride | HCID 2735913 | — |
| Reactant | 5-(4-Chlorophenyl)-2-(trifluoromethyl)furan-3-carbonyl chloride | HCID 2736641 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 54761408 | HCID 54761408 | 26.1% |
Reaction Steps
5-(4-Chloro-phenyl)-2-trifluoromethyl-furan-3-carbonyl chloride (0.200 g) was added to a solution of 3-fluoro-5-trifluoromethyl-phenylamine (0.105 g) and N,N-diisopropylethylamine (0.102 mL) in dichloromethane (5 mL). After stirring at room temperature for 1 day, the reaction underwent an aqueous acidic (dilute HCl, 2×15 mL) and basic (dilute NaHCO3, 2×15 mL) workup followed by washing with brine (saturated NaCl, 2×15 mL), drying over MgSO4, and concentration. The crude compound was triturated with hexanes/ethyl ether (1:1) to afford the title compound (0.069 g, 24% yield). 1H NMR (CDCl3) δ 7.69 (d, 1H, J=0.02 Hz), 7.68 (s, 1H), 7.67 (d, 2H, J=0.017 Hz), 7.53 (s, 1H), 7.47 (d, 2H, J=0.017 Hz), 7.16 (d, 1H, J=0.02 Hz), 7.02 (s, 1H). ES-MS negative Q1 (m/z) 451.
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-e22c59716a134358882787c6f841e53b |
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| Source note | uspto-grants-2014_05 |
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