반응 #85707

반응 방정식

1H-imidazole-4-carbaldehyde

1-chloro-4-iodobenzene

(1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine

cesium carbonate

→

1-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde

수율 107.3%

용매

DMF

NH4Cl

반응 조건

후처리

1. 1
   기타The reaction was sealed
2. 2
   온도The reaction mixture was then cooled to room temperature
3. 3
   기타Solid was collected
4. 4
   세척washed with water and air
5. 5
   기타dried
6. 6
   workup.DISSOLUTIONSolid material was then dissolved in 10% MeOH
7. 7
   건조90% DCM solution and dried (Na2SO4)
8. 8
   여과filtered
9. 9
   농축concentrated

실험 절차

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.

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