関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | 1-Chloro-4-iodobenzene | HCID 12510 | — |
| 反応物 | 1H-Imidazole-4-carbaldehyde | HCID 76428 | — |
| 反応物 | trans-N,N'-dimethyl-1,2-cyclohexanediamine | HCID 2733821 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Ammonium Chloride | HCID 25517 | — |
| 生成物 | 1-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde | HCID 83883034 | 107.3% |
反応手順
To a mixture of 1H-imidazole-4-carbaldehyde (3.71 g, 38.6 mmol), 1-chloro-4-iodobenzene (13.81 g, 57.9 mmol), (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (1.10 g, 7.72 mmol), copper(I) iodide (0.368 g, 1.93 mmol) and cesium carbonate (25.2 g, 77 mmol) was added DMF (50 mL). The reaction was sealed and heated to 110° C. for 18 hours. The reaction mixture was then cooled to room temperature and diluted with a saturated solution of NH4Cl. A brown solid develops. Solid was collected, washed with water and air dried. Solid material was then dissolved in 10% MeOH:90% DCM solution and dried (Na2SO4), filtered and concentrated to afford a dark brown solid 1-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde (8.55 g, 41.4 mmol, 107% yield). Material as used without further purification. LCMS m/z 207.1 (M+H)+, Rt 0.58 min.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09434719B2 |
|---|
| 出典データセット | uspto-grants-2016_09 |
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| ORD ID | ord-3afaac30416d41f195407537c5aa6443 |
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| 出典メモ | uspto-grants-2016_09 |
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