Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | 1-Methyl-2-imidazolecarboxaldehyde | HCID 139575 | — |
| Reactant | Sodium ethoxide | HCID 2723922 | — |
| Reactant | HCID 178484454 | HCID 178484454 | — |
| Solvent | Ethyl Propionate | HCID 7749 | — |
| Product | HCID 67259096 | HCID 67259096 | 30% |
Reaction Steps
A mixture of compound 1-methyl-1H-imidazole-2-carbaldehyde (110 mg, 1.0 mmol) and (E)-2-fluoro-N,N-dimethyl-5-((1-oxo-1,3-dihydroisobenzofuran-4-ylimino)methyl)benzamide (300 mg, 0.92 mmol) in ethyl propionate (10 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (85 mg, 3.68 mmol) in ethanol (5 mL)) was added dropwise. After the addition, the mixture was stirred at room temperature for 2.5 hr. The mixture was quenched with water (20 mL) and solvent was removed in vacuum. The residue was dissolved in water and extracted with ethyl acetate three times, washed by water, brine then the extraction was evaporated, the crude product was purified by chromatography to obtain a yellow solid. The solid was dried in vacuum at 50° C. to give the title compound (130 mg, yield: 30%). LC-MS (ESI) m/z: 465 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08012976B2 |
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| Source dataset | uspto-grants-2011_09 |
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| ORD ID | ord-6e66e23547d64f68abc9c5a47735268d |
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| Source note | uspto-grants-2011_09 |
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