Reaktion #553043

Reaktionsgleichung

2-n-Butyl-4-chloroimidazole-5-carboxaldehyde

4-bromomethyl-2'-cyanobiphenyl

potassium carbonate

→

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)methyl]imidazole-5-carboxaldehyde

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe solids were filtered
2. 2
   Sonstigethe filtrate evaporated
3. 3
   SonstigeThe residue was chromatographed over silica gel in 9:1 to 1:1 hexane/ethyl acetate
4. 4
   Sonstigecrystallized from methylcyclohexane/n-butyl chloride yielding 9.70 g of a solid

Vorschrift

2-n-Butyl-4-chloroimidazole-5-carboxaldehyde (6.34 g, 34.0 mmol, 1 eq.), 4-bromomethyl-2'-cyanobiphenyl (9.25 g, 34.0 mmol, 1 eq.), potassium carbonate (5.17 g, 37.4 mmol, 1.1 eq.) and DMF (100 mL) were mixed and stirred at 25° C. overnight. The solids were filtered and the filtrate evaporated. The residue was chromatographed over silica gel in 9:1 to 1:1 hexane/ethyl acetate and crystallized from methylcyclohexane/n-butyl chloride yielding 9.70 g of a solid; m.p. 96.0°-97.0° C. NMR (CDCl3): δ9.78 (s, 1H); 7.83-7.40 (m, 6H); 7.19 (d, 2H, J=9 Hz); 5.63 (s, 2H); 2.71 (t, 2H, J=7 Hz); 1.72 (t of t, 2H, J=7,7 Hz); 1.38 (t of q, 2H, J=7,7 Hz); 0.90 (t, 3 H, J=7 Hz). Anal calcd. for C22H20ClN3O: C, 69.93; H, 5.34; N, 11.12. Found: C, 69.64; H, 5.37; N, 11.21.

Quelle