関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | 3-Bromobenzene-1-sulfonamide | HCID 2734765 | — |
| 反応物 | 6-Bromohexylbut-3-ynyl ether | HCID 11379281 | — |
| 触媒 | Triphenylphosphine | HCID 11776 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 3-[4-[(6-Bromohexyl)oxy]but-1-ynyl}benzenesulfonamide | HCID 21895558 | 90.7% |
反応手順
A mixture of 3-bromo-benzenesulfonamide (625 g), 6-bromohexyl but-3-ynyl ether (850.1 g), bis(triphenylphosphine)palladium (II) chloride (62.5 g), triphenylphosphine (18.1 g) and triethylamine (536.3 g) in tetrahydrofuran (6250 ml) was stirred under an atmosphere of nitrogen for 20 min. Copper (I) iodide (12.5 g) was then added to give a dark red/brown mixture that was heated to 50° C. for 23 h. The reaction mixture was then cooled to room temperature and filtered through a short silica pad (1000 g). The pad was washed with additional tetrahydrofuran (15.6L) and the resulting solution then concentrated under reduced pressure to give crude product (1382 g) as a viscous oil. This was purified by chromatography (7 kg silica) eluting with petroleum ether-ethyl acetate (5:1) followed by petroleum ether-ethyl acetate (2:1) to give the title compound (932.9 g) as an oil, LC RT=5.69 min.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07402598B2 |
|---|
| 出典データセット | uspto-grants-2008_07 |
|---|
| ORD ID | ord-5a7b2cd47f7f43738379bbc82be57700 |
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| 出典メモ | uspto-grants-2008_07 |
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