Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 18948960 | HCID 18948960 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 9804615 | HCID 9804615 | 85.3% |
Reaction Steps
Triethylamine (0.17 ml, 1.2 mmol) was added to benzylamine (117.9 mg, 1.1 mmol) dissolved in tetrahydrofuran (5 ml). After the solution was cooled in the ice bath, 5-{[(4-methylphenyl)sulfonyl]oxy}naphthalene-1-sulfonyl chloride (396.9 mg, 1.2 mmol) was added, and the mixture was stirred at room temparature for 1 hour. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (eluent; n-hexane : ethyl acetate=2:1) and crystallized (ethyl acetate/hexane) to give the title compound as a white crystal (398.8 mg, 85.3%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07598418B2 |
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| Source dataset | uspto-grants-2009_10 |
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| ORD ID | ord-3d92748b370c479babb52ac8e8f208ee |
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| Source note | uspto-grants-2009_10 |
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