1,1'-Carbonyldiimidazole → HCID 9931208, compound

Participants

Reaction Steps

A suspension of 4-amino-5-chloro-2-[(2-methylthiazol-4-yl)methoxy]benzoic acid (1.54 g, 5 mmoles) in anhydrous tetrahydrofuran (5 ml) was treated with 1,1'-carbonyldiimidazole (0.89 g, 5.5 mmoles), stirred at room temperature for 90 minutes, then added to a cooled (0° C.) solution of 3-aminoquinuclidine (from 6 mmoles of dihydrochloride salt and 12 mmoles of 25% sodium methoxide/methanol) in anhydrous tetrahydrofuran (5 ml) under nitogen. After 3 hours at room temperature and one hour at 60° C., the solution was concentrated in vacuo and partitioned between methylene chloride (50 ml) and 1.5N sodium hydroxide (20 ml). The organic layer was washed with 1.5N sodium hydroxide (20 ml), saturated sodium bicarbonate (20 ml), and brine (20 ml), dried (Na2SO4), and concentrated in vacuo. Filtration through alumina (eluted with 10% methanol/methylene chloride) provided 1.35 g (66%) of a colorless foam.

Provenance & Evidence