Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 178498365 | HCID 178498365 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69356079 | HCID 69356079 | 61% |
Reaction Steps
To a solution of ethyl methyl 4-(2-oxo-1-pyrrolidinyl)-1H-1,2,3-benzotriazole-6-carboxylate (D249) (400 mg, 1.54 mmol, 1 equiv) in DMF (10 ml) at room temperature was added NaH (60% dispersion in mineral oil, 68 mg, 1.69 mmol, 1.1 equiv) and the resulting mixture was stirred 5 min at this temperature. Ethyl iodide (135 μl, 1.69 mmol, 1.1 equiv) was added and the resulting solution was stirred for 2 h then concentrated in vacuo. The residue was dissolved in AcOEt and the organic phase was washed with H2O, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 100/0) gave methyl 1-ethyl-4-(2-oxo-1-pyrrolidinyl)-1H-1,2,3-benzotriazole-6-carboxylate (270 mg, 61%) as a pale yellow oil. [M+H]+=289.3, RT=2.47 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07253198B2 |
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| Source dataset | uspto-grants-2007_08 |
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| ORD ID | ord-e7302d7b634242268d13345187b1c2b9 |
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| Source note | uspto-grants-2007_08 |
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