Sodium hydride → HCID 53893541, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (50% dispersion in oil, 1.37 g, 28.6 mmol, 1.1 eq) was added to a DMF solution (50 mL) containing 2-n-butyl-4-chloroimidazole-5-carboxaldehyde (prepared as in European Patent Application Number 89100144.8, published 7.19.89) (4.85 g, 26.0 mmol, 1.0 eq). The contents were heated with stirring at 60° C. until everything was dissolved. The reaction was then cooled to 0° C. and a DMF solution (75 mL) of 2-bromomethylanthracene (entire contents from the previous step: 7.77 g of impure material, theoretically 26.0 mmol, 1.0 eq) was added and the entire contents stirred at room temperature overnight. The solvent was removed in vacuo and the residue flash chromatographed in 9:1 toluene/ethyl acetate to 75:25 toluene/ethyl acetate to yield 3.73 g of an amber glass. This material could not be crystallized and was used without further purification for the next step. NMR (CDCl3): δ 9.80 (s, 1H); 8.40 (s, 1H); 8.33 (s, 1H); 7.98 (m, 3H); 7.48 (m, 3H); 7.23 (m, 1H); 5.72 (s, 2H); 2.79 (t, 2H, J=7Hz); 1.69 (t of t, 2H, J=7,7Hz); 1.33 (t of q, 2H, J=7,7Hz); 0.84 (t, 3H, J=7Hz). ##STR56##

Provenance & Evidence