Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Nitrophenyl chloroformate | HCID 82129 | — |
| Reactant | 3-Methyl-5-(trifluoromethyl)aniline hydrochloride | HCID 86655666 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68320915 | HCID 68320915 | 98.9% |
Reaction Steps
3-Methyl-5-(trifluoromethyl)aniline monohydrochloride (2.93 g) synthesized in reference to a known method (U.S. Pat. No. 4,532,353) was dissolved in THF (25 mL), and 4-nitrophenyl chlorocarbonate (3.07 g) and N,N-diisopropylethylamine (1.97 mL) were added dropwise at 5° C. The reaction mixture was stirred at 5° C. for 1 hr, poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried and concentrated under reduced pressure to give the title compound (4.66 g) as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08592454B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-567a16b07d4f48649a629d309bec7986 |
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| Source note | uspto-grants-2013_11 |
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