반응 #52117

반응 방정식

(R)-3-(4-Bromobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-α]-imidazol-2-one

CuCN

→

(R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-a)-imidazol-2-one

수율 77.4%

용매

DMF

반응 조건

후처리

1. 1
   기타the solvent was removed under reduced pressure
2. 2
   workup.ADDITIONthe residue was diluted with CH2Cl2
3. 3
   세척The organic solution was washed four times alternately with 5% aqueous pyridine
4. 4
   건조The organic layer was dried over Na2SO4
5. 5
   여과filtered through a diatomaceous earth pad
6. 6
   농축The filtrate was concentrated
7. 7
   기타purified by silica gel column chromatography
8. 8
   workup.ADDITIONa mixture of CH2Cl2-hexane (10:1) as an eluent

실험 절차

(R)-3-(4-Bromobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-α]-imidazol-2-one (13.5 g, 29.9 mmol) was dissolved in anhydrous DMF (70 mL) and CuCN (3.22 g, 35.9 mmol) was added. The reaction mixture was heated to 140° C. under argon for 40 h. When the reaction was complete, the solvent was removed under reduced pressure and the residue was diluted with CH2Cl2. The organic solution was washed four times alternately with 5% aqueous pyridine then water. The organic layer was dried over Na2SO4 and filtered through a diatomaceous earth pad. The filtrate was concentrated and purified by silica gel column chromatography using a mixture of CH2Cl2-hexane (10:1) as an eluent to afford 9.19 g of (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-a)-imidazol-2-one.

출처