関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Benzyl mercaptan | HCID 7509 | — |
| 反応物 | 1,4-Dioxane | HCID 31275 | — |
| 反応物 | 4-Bromo-2-nitroaniline | HCID 70132 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 触媒 | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 溶媒 | Water | HCID 962 | — |
| 生成物 | 4-(Benzylthio)-2-nitroaniline | HCID 13550993 | 88.2% |
反応手順
A screw cap vial was charged with 4-bromo-2-nitroaniline (7.00 g, 32.3 mmol), xantphos (0.933 g, 1.613 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.738 g, 0.806 mmol), 1,4-Dioxane (32.3 ml), and DIPEA (11.22 ml, 64.5 mmol). The vial was purged with Argon, sealed and heated to 80° C. for 10 minutes. The reaction was cooled to room temperature and benzyl mercaptan (4.01 ml, 33.9 mmol) was added and the reaction heated at 80° C. for 3 hours. The reaction was cooled to room temperature, diluted with water and extracted with DCM (3×). The combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The resulting material was concentrated, dissolved in minimal DCM and purified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane) to afford 4-(benzylthio)-2-nitroaniline (7.43 g, 28.5 mmol, 88% yield). m/z (ESI) 261.2 (M+H)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09212182B2 |
|---|
| 出典データセット | uspto-grants-2015_12 |
|---|
| ORD ID | ord-1e006f5cddc94ebfac893136c2591d2d |
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| 出典メモ | uspto-grants-2015_12 |
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