Reaktion #85707

Reaktionsgleichung

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

Ausbeute 107.3%

Lösungsmittel

DMF

NH4Cl

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was sealed
2. 2
   TemperaturThe reaction mixture was then cooled to room temperature
3. 3
   SonstigeSolid was collected
4. 4
   Waschenwashed with water and air
5. 5
   Sonstigedried
6. 6
   workup.DISSOLUTIONSolid material was then dissolved in 10% MeOH
7. 7
   Trocknen90% DCM solution and dried (Na2SO4)
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated

Vorschrift

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.

Quelle