HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-{3-[(7-Bromoheptyl)oxy]prop-1-ynyl}benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Bromobenzene-1-sulfonamide | HCID 2734765 | — |
| Reactant | 1-Bromo-7-(prop-2-yn-1-yloxy)heptane | HCID 21895540 | — |
| Catalyst | Triphenylphosphine | HCID 11776 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-{3-[(7-Bromoheptyl)oxy]prop-1-ynyl}benzenesulfonamide | HCID 21895385 | 46.1% |
Reaction Steps
7-Bromoheptyl prop-2-ynyl ether (55.1 g) in THF (250 ml) was added dropwise over ca 8 h to a stirred mixture of 3-bromobenzenesulfonamide (43.5 g), PdCl2(PPh3)2 (6.48 g), PPh3 (1.45 g), CuI (1.4 g) and Et3N (52 ml) in THF (250 ml) at 55±5° C. under nitrogen then the mixture heated for a further ca 15 hrs. The reaction was cooled, filtered through Celite and the solids washed with THF. The solution was concentrated and the product purified by chromatography on flash silica gel (600 g) eluting with petroleum ether:ethyl acetate (ratios ranging successively from 19:1 to 7:3) to give the title compound (33 g)—LC RT=5.85 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07442837B2 |
| Source dataset | uspto-grants-2008_10 |
| ORD ID | ord-c0dcccc5d2c64083891ac1e1b32325bd |
| Source note | uspto-grants-2008_10 |