Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylenediamine | HCID 3301 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | (5-Bromo-1-benzofuran-2-yl)methanol | HCID 2795537 | — |
| Reactant | HCID 178418546 | HCID 178418546 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 12813635 | HCID 12813635 | 74% |
Reaction Steps
A solution of 5-bromo-2-benzofuranylmethanol (1.19 g, 5.24 mmol), copper (I) cyanide (0.470 g, 5.25 mmol) and N-methylpyrrolidinone (15 ml) was left under stirring at 200° C. for 3.5 h, then was poured onto a solution of ethylenediamine (6 g) in water (80 ml) and extracted with ethyl acetate (3×75 ml). The organic phase was dried and the solvents were evaporated off under reduced pressure. The resulting crude was purified by chromatography through a silica gel column, eluting with n-hexane:ethyl acetate mixtures of increasing polarity, thereby obtaining 0.671 g of title product as a yellow solid with melting point 113-114° C. (74% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05990142 |
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| Source dataset | uspto-grants-1999_11 |
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| ORD ID | ord-adbacfefd2514e7a80d62e362bb51d99 |
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| Source note | uspto-grants-1999_11 |
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