HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-Fluoro-N-methyl-2-nitrobenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 5-Fluoro-2-nitrobenzoic acid | HCID 2737420 | — |
| Reactant | Methylamine hydrochloride | HCID 6364545 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-Fluoro-N-methyl-2-nitrobenzamide | HCID 44203077 | 90% |
Reaction Steps
A mixture of 5-fluoro-2-nitrobenzoic acid (4.775 g, 25.8 mmol), methylamine hydrochloride (2.626 g, 38.9 mmol), EDCI (5.982 g, 31.2 mmol), HOBt (4.227 g, 31.3 mmol) and triethylamine (7.2 mL, 51.65 mmol) in DMF (50 mL) was stirred at room temperature for 24 h. It was diluted with ethyl acetate and washed with saturated sodium bicarbonate, brine and dried over magnesium sulfate. The solvent was removed and the residue was purified by silica gel chromatography (combiflash-companion; ethyl acetate/hexanes gradient) to give the title compound as a yellow solid (yield: 90%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08501763B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-31fe7eb1ca1d49fdba29f3ea71d06dab |
| Source note | uspto-grants-2013_08 |