Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 3-Bromo-2-chlorobenzoic acid | HCID 33124 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86028266 | HCID 86028266 | 84.5% |
Reaction Steps
500 mg of 3-bromo-2-chlorobenzoic acid are placed in 12.5 ml of tetrahydrofuran in a round-bottomed flask. The reaction mixture is cooled to 0° C. with an ice bath and then 228 mg of N,O-dimethylhydroxylamine hydrochloride, 814 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.21 ml of pyridine are added thereto. The reaction mixture is subsequently stirred at ambient temperature for 16 h and the solvent is evaporated under reduced pressure. The residue is taken up between water and dichloromethane. The separated organic phase is subsequently washed once with a saturated ammonium chloride solution and once with a saturated sodium hydrogencarbonate solution, then dried over magnesium sulphate and concentrated under reduced pressure. 500 mg of compound are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08148370B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-5acaa99a930346fe85b5d77528dbcd4e |
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| Source note | uspto-grants-2012_04 |
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