Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 86632930 | HCID 86632930 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 68764688 | HCID 68764688 | 98.6% |
Reaction Steps
A mixture of the resulting thiourea (22.0 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (8.49 g, 44.3 mmol), and triethylamine (6.2 mL) in tetrahydrofuran (150 mL) was stirred at 50° C. for 15 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with n-hexane to give methyl 4-chloro-2-{[4-chloro-2-(trifluoromethyl)phenyl]amino}-1-(3-hydroxypropyl)-1H-benzimidazole-7-carboxylate as a brown powder (20.2 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08785460B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-3353a2247171453b883d7833147a9d10 |
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| Source note | uspto-grants-2014_07 |
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