참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Cesium carbonate | HCID 10796 | — |
| 반응물 | 1-Chloro-4-iodobenzene | HCID 12510 | — |
| 반응물 | 1H-Imidazole-4-carbaldehyde | HCID 76428 | — |
| 반응물 | trans-N,N'-dimethyl-1,2-cyclohexanediamine | HCID 2733821 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 용매 | Ammonium Chloride | HCID 25517 | — |
| 생성물 | 1-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde | HCID 83883034 | 107.3% |
반응 단계
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.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US09434719B2 |
|---|
| 출처 데이터셋 | uspto-grants-2016_09 |
|---|
| ORD ID | ord-3afaac30416d41f195407537c5aa6443 |
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| 출처 메모 | uspto-grants-2016_09 |
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