1,1'-Carbonyldiimidazole → HCID 20454780, compound

Participants

Reaction Steps

To a cooled solution of 15.00 g (67 mmole) of N-(2-amino-6-methylbenzyl) glycine ethyl ester (10b) in 300 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere was added a solution of 11.72 g (72 mmole) of 1,1'-carbonyldiimidazole in 200 ml of anhydrous tetrahydrofuran at such a rate that the temperature did not exceed 5°. Upon complete addition, the solution was allowed to stir at room temperature for 2 hrs., heated to reflux for 18 hrs., cooled to room temperature and the tetrahydrofuran removed in vacuo. The residue was dissolved in methylene chloride (250 ml), washed with 5% aqueous hydrochloric acid (2×100 ml), then water (100 ml). The methylene chloride extract was dried (Na2SO4) and the solvent removed in vacuo affording 14.0 g (83% yield) of a colorless solid. Purification was effected by crystallization from nitromethane; m.p. 184°-5°.

Provenance & Evidence