Reaction #2443

Reaction equation

potassium carbonate

2-butyl-4-iodoimidazole-5-carboxaldehyde

methyl 4-bromomethylnaphthalene-1-carboxylate

water

→

solid

Yield 85.0%

Methyl 4-[(2-n-Butyl-5-formyl-4-iodo-1H-imidazol-5-yl)methyl]-1-napthalene carboxylate

Yield 85.0%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Otherthe solid which separated
2. 2
   Filtrationwas collected by filtration
3. 3
   Washwashed with water
4. 4
   Othertriturated several times with 250 ml of boiling methanol

Procedure

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 mixture was poured into water and the solid which separated 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.

Source