Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylamine, hydrochloride | HCID 10473 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 5-Bromo-2-fluorobenzoic acid | HCID 2736315 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 21196241 | HCID 21196241 | 100% |
Reaction Steps
5-Bromo-2-fluorobenzoic acid (500 mg, 2.23 mmol) was dissolved in DMF (5.0 mL), and dimethylamine hydrochloride (223 mg, 2.72 mmol), WSC.HCl (511 mg, 2.66 mmol), HOBt.H2O (410 mg, 2.68 mmol), and potassium carbonate (367 mg, 2.66 mmol) were added thereto, and the mixture was stirred at room temperature for 3 hours. To the mixture, an aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50) to give 5-bromo-2-fluoro-N,N-dimethylbenzamide (550 mg, 2.23 mmol, yield: 99%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08273738B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-74a7fc93c782410baffad9292a6319d6 |
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| Source note | uspto-grants-2012_09 |
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