Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | N-(2-aminoethyl)-N-(4-nitrophenyl)amine | HCID 236318 | — |
| Reactant | 2-Trifluoromethanesulfonyloxy-4,6-dimethylpyridine | HCID 57668797 | — |
| Solvent | Diglyme | HCID 8150 | — |
| Product | HCID 66850960 | HCID 66850960 | 55% |
Reaction Steps
To a solution of trifluoro-methanesulfonic acid 4,6-dimethyl-pyridin-2-yl ester (prepared according to J. Org. Chem., 63, 10048-51, 1998), using pyridine as base. 0.6 g, 2.35 mmol) in diglyme (2 mL) was added N*1*-(4-nitro-phenyl)-ethane-1,2-diamine (0.51 g, 2.82 mmol). The reaction mixture was heated to 165° C. for 24 h. The resulting reaction mixture was concentrated under reduced pressure and the residue diluted with chloroform. The organic layer was washed with brine and water and dried over sodium sulfate. The solvent was evaporated and the crude residue was purified by column chromatography (60-120 mesh) using 20% ethyl acetate/petroleum ether as eluent to afford N-(4,6-dimethyl-pyridin-2-yl)-N′-(4-nitro-phenyl)-ethane-1,2-diamine (0.38 g, 55%) as a cream solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08524705B2 |
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| Source dataset | uspto-grants-2013_09 |
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| ORD ID | ord-49b7de1260744140b91394a6f3c7317b |
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| Source note | uspto-grants-2013_09 |
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