Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1-Methylimidazole | HCID 1390 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methyl 2-amino-5-bromobenzoate | HCID 736224 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 66680112 | HCID 66680112 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 66680548 | HCID 66680548 | 81% |
Reaction Steps
Under ice-cooling, 1.53 g (7.97 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a DMAc (5 mL) solution comprising 1.45 g (6.64 mmol) of [3-(furan-3-yl)phenoxy]acetic acid, 1.60 g (6.97 mmol) of methyl 2-amino-5-bromobenzoate, and 1.08 g (7.97 mmol) of 1-hydroxybenzotriazole, and the mixture was stirred at room temperature for 4 hours. Under ice-cooling, 1.63 g (19.9 mmol) of 1-methylimidazole was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was stirred for 1 hour. The precipitates were collected by filtration and washed with water and IPE, followed by drying under reduced pressure at 50° C. for 3 hours, thereby giving 2.30 g of methyl 5-bromo-2-({[3-(furan-3-yl)phenoxy]acetyl}amino)benzoate (yield: 81%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08785473B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-ec82b77a04664b03a3db505c70407137 |
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| Source note | uspto-grants-2014_07 |
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