Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 2,3-Dichloro-4-fluorobenzoic acid | HCID 10330705 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59370537 | HCID 59370537 | 81.5% |
Reaction Steps
A solution of 2,3-dichloro-4-fluorobenzoic acid (0.200 g, 0.92 mmol) in dichloromethane (˜4 ml) was treated with 1-hydroxybenzotriazole (0.162 g, 1.2 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.230 g, 1.2 mmol), and triethylamine (0.56 ml, 4.0 mmol) under argon at room temperature. The mixture was stirred at room temperature for 40 minutes then treated with) 32% aqueous ammonium hydroxide (0.088 ml) and stirred overnight at room temperature. The mixture was diluted with dichloromethane and washed sequentially with water and then with saturated aqueous sodium hydrogen carbonate. The organic layer was separated and dried over sodium sulphate then concentrated to give 2,3-dichloro-4-fluorobenzamide (0.156 g) as a white solid that was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08048907B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-bc03d42c624c462889cc9af4286ff00a |
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| Source note | uspto-grants-2011_11 |
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