Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 3-Bromo-5-iodobenzoic acid | HCID 5182520 | — |
| Reactant | Methylamine hydrochloride | HCID 6364545 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22341476 | HCID 22341476 | 96% |
Reaction Steps
37.5 g (115 mmol) of 3-bromo-5-iodobenzoic acid in 300 ml of dimethylformamide are introduced into a round-bottomed flask under a stream of nitrogen. 17.6 ml (127 mmol) of triethylamine, 17 g (126 mmol) of 1-hydroxybenzotriazole and 7.75 g (115 mmol) of methylamine hydrochloride are added. The reaction medium is cooled to 0° C., followed by portionwise addition of 24.2 g (126 mmol) of 1-[3-(dimethyl-amino)propyl]-3-ethylcarbodiimide hydrochloride. The medium is allowed to warm to room temperature and is stirred for 18 hours. It is then poured into water and the precipitate obtained is filtered off, washed with heptane and then dried. 37.3 g (96%) of the expected product are obtained in the form of a beige-colored powder with a melting point of 205° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06927228B2 |
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| Source dataset | uspto-grants-2005_08 |
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| ORD ID | ord-056323976f24450392432941d285bfa7 |
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| Source note | uspto-grants-2005_08 |
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