Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Benzeneamine, 4,4',4''-methylidynetris- | HCID 68356 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 22490733 | HCID 22490733 | 44% |
Reaction Steps
Tris(4-aminophenyl)methane (2.9 g), formic acid (4.6 g) and 4-dimethylaminopyridine (122 mg) were dissolved in dichloromethane (30 ml), after which 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (9.61 g) was added under a nitrogen atmosphere at 5° C., the temperature was raised to room temperature, and the mixture was stirred for 2 days. Ethyl acetate (100 ml) and water (50 ml) were added to the reaction mixture which was then vigorously shaken, and the organic layer was washed with saturated sodium bicarbonate water (20 ml), water (20 ml) and saturated aqueous sodium chloride (20 ml), dried over sodium sulfate, and concentrated to dryness. The residue was purified by silica gel column chromatography (Kieselgel 60, 240-400 mesh) and elution was performed with a mixed solvent of chloroform:methanol=90:10 to obtain 1.63 g of the title compound as a light brown powder (44% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06887890B2 |
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| Source dataset | uspto-grants-2005_05 |
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| ORD ID | ord-268da54416a24a9e9772d9cac32a3eae |
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| Source note | uspto-grants-2005_05 |
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