関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Acetamide | HCID 178 | — |
| 反応物 | 1,2-Diaminocyclohexane, trans- | HCID 43806 | — |
| 反応物 | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 反応物 | o-Iodoanisole | HCID 68257 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | Acetamide, N-(2-methoxyphenyl)- | HCID 7135 | 94.3% |
反応手順
An oven-dried resealable Schlenk tube was charged with CuI (2.0 mg, 0.0105 mmol, 1.0 mol %), acetamide (180 mg, 3.05 mmol), K3PO4 (450 mg, 2.12 mmol), evacuated and backfilled with argon. trans-1,2-Cyclohexanediamine (13 μL, 0.108 mmol, 10 mol %), 2-iodoanisole (135 μL, 1.04 mmol) and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 90° C. for 23 h. The resulting light green suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 2:3; 20 mL fractions). Fractions 10-16 provided 162 mg (94% yield) of the product as white crystals. The 1H NMR spectrum was in accord with that reported. Hibbert, F.; Mills, J. F.; Nyburg, S. C.; Parkins, A. W. J. Chem. Soc., Perkin Trans. 1 1998, 629.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US06867298B2 |
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| 出典データセット | uspto-grants-2005_03 |
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| ORD ID | ord-56514ccc60874326a4f574d931f65abf |
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| 出典メモ | uspto-grants-2005_03 |
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