تفاعل #85707

معادلة التفاعل

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

المردود 107.3%

المذيبات

DMF

NH4Cl

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was sealed
2. 2
   درجة الحرارةThe reaction mixture was then cooled to room temperature
3. 3
   أخرىSolid was collected
4. 4
   غسيلwashed with water and air
5. 5
   أخرىdried
6. 6
   workup.DISSOLUTIONSolid material was then dissolved in 10% MeOH
7. 7
   تجفيف90% DCM solution and dried (Na2SO4)
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated

الإجراء التجريبي

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.

المصدر