Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Bromide | HCID 6332 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 73128510 | HCID 73128510 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 73128509 | HCID 73128509 | 49.7% |
Reaction Steps
5-[3-(3-Bromo-4-ethoxy-phenyl)-1-phenyl-1H-pyrazol-4-yl-methylene]-thiazolidine-2,4-dione (Compound No. 77, 0.10 mg, 0.21 mmol) was dissolved in 1.00 mL of anhydrous dimethylformamide. Sodium hydride (12.74 mg, 0.32 mmol) was added under nitrogen atmosphere and bromoethane (23.72 μL, 0.32 mmol) was added 5 minutes later. The mixture was stirred at room temperature for 2 hours. When the reaction was completed, 10 mL of water was added and the solution was extracted with dichloromethane (10 mL×2 times). The organic layer was washed with brine and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The product was purified with silica gel chromatography (n-hexane/ethyl acetate=4:1) to obtain 52 mg (49.2%) of the target product in yellow solid form.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07718681B2 |
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| Source dataset | uspto-grants-2010_05 |
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| ORD ID | ord-469c3cb2579b4a6d8e232c043fcb12d1 |
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| Source note | uspto-grants-2010_05 |
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