Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1H-Imidazole-4-carbaldehyde | HCID 76428 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-ETHYL-3H-IMIDAZOLE-4-CARBALDEHYDE | HCID 3159672 | 30% |
| Product | 1-Ethyl-1H-imidazole-4-carbaldehyde | HCID 13509872 | 9% |
Reaction Steps
1H-Imidazole-5-carbaldehyde (300 mg, 3.12 mmol) was dissolved in N,N-dimethylformamide (4 mL). To this, potassium carbonate (862 mg, 6.24 mmol) and ethyl iodide (0.275 mL, 3.43 mmol) were added at room temperature and the mixture was stirred at the same temperature for 1.5 hours. After water was added to the reaction mixture, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1) to give 1-ethyl-1H-imidazole-5-carbaldehyde (115 mg, yield: 30%) and 1-ethyl-1H-imidazole-4-carbaldehyde (36 mg, yield: 9%). 1-ethyl-1H-imidazole-5-carbaldehyde
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08673908B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-4e89b32c2f034fbdb8b166bf66a9ba3b |
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| Source note | uspto-grants-2014_03 |
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