Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Bis(2-chloroethyl) ether | HCID 8115 | — |
| Reactant | HCID 67406226 | HCID 67406226 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 67407516 | HCID 67407516 | 24% |
Reaction Steps
2-Chloro-6-trifluoromethyl-benzene-1,4-diamine (2.9 g), bis-(2-chloroethyl)ether (1.7 mL) and sodium iodide (516 mg) were mixed in acetonitrile (45 mL) and heated to 165° C. for 1 hour in a sealed microwave process vessel. The crude mixture was concentrated in vacuo, redissolved in ethyl acetate (100 mL) and washed with water (2×100 mL) and brine (1×100 mL). The organic phase was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 940 mg (24%) of the title compound as a black oil. 1H NMR (500 MHz, CDCl3): 3.02 (m, 4H), 3.84 (m, 4H), 4.30 (b, 2H), 6.97 (d, 1H), 7.06 (d, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07812023B2 |
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| Source dataset | uspto-grants-2010_10 |
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| ORD ID | ord-375f164276594e5d8e0c6a29bb22bc7a |
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| Source note | uspto-grants-2010_10 |
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