Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Benzenamine, N-methyl-2-nitro- | HCID 69157 | — |
| Reactant | 2,3-Dichloropyrazine | HCID 78575 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 18670519 | HCID 18670519 | 22.2% |
Reaction Steps
To a solution of 1.52 g of N-methyl-2-nitroaniline in N,N-dimethylformamide (50 ml) was added in a nitrogen atmosphere 0.44 g of sodium hydride. After stirring for 30 minutes, 1.75 g of 2,3-dichloropyrazine was added thereto and the resulting mixture was stirred at room temperature for additional 6 hours. Then the reaction mixture was distributed into ethyl acetate and a saturated aqueous solution of sodium dihydrogenphosphate and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed successively with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 0.586 g of the title compound as an oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06518423B1 |
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| Source dataset | uspto-grants-2003_02 |
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| ORD ID | ord-ae513f77cb1e46a68e725cab20f18340 |
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| Source note | uspto-grants-2003_02 |
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