Reaktion #65283

Reaktionsgleichung

potassium carbonate

2-butyl-4-iodoimidazole-5-carboxaldehyde

methyl 4-bromomethylnaphthalene-1-carboxylate

water

→

solid

Ausbeute 85.2%

methyl-4-[(2-butyl-5-formyl-4-iodo-1H-imidazol-1-yl)methyl]naphthalene-1-carboxylate

Ausbeute 85.2%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe resulting solid was collected by filtration
2. 2
   Waschenwashed with water
3. 3
   Sonstigetriturated several times with 250 mL of boiling methanol

Vorschrift

A suspension of 29.53 g (0.214 mol) of powdered potassium carbonate, 60.00 g (0.214 mol) of 2-butyl-4-iodoimidazole-5-carboxaldehyde and 65.68 g (0.235 mol) of methyl 4-bromomethylnaphthalene-1-carboxylate (E. A. Dixon, A. Fischer, and F. P. Robinson, Can. J. Chem, 59, 2629 (1981)) in 600 mL of dimethylformamide was stirred for 5 hours under argon at 70° C. An additional 6.56 g (0.0235 mol) of the bromomethyl ester was added and the suspension was stirred an additional 15 hours at 70° C. The reaction mixture was poured into water and the resulting solid was collected by filtration, washed with water, and triturated several times with 250 mL of boiling methanol to give 86.8 g (85%) of a solid; mp 177.5°-179° C.

Quelle