Water → HCID 22449795, compound

Participants

Reaction Steps

(Method 2) Ethyl 2-(2-aminobenzamide)isobutyrate (6.98 g, 27.9 mmol) obtained in Reference Example 19 was dissolved in pyridine (30 ml) and treated dropwise with ethyl chloroformate (2.94 ml, 30.7 mmol) with cooling on ice and stirring. The reaction mixture was stirred at room temperature for 2 hours, combined with water and then extracted with ethyl acetate. The extract was washed with an aqueous solution of potassium hydrogen sulfate followed by saturated brine, and dried (MgSO4), and then the solvent was distilled off under reduced pressure. The residue was taken up with ethanol (150 ml) and combined with sodium ethylate (2.09 g, 30.7 mmol) and heated under reflux for 15 hours. The solvent was distilled off under reduced pressure and the residue was diluted with water and neutralized with 1N hydrochloric acid. The crystal precipitated was recovered by filtration to give the title compound (6.57 g, 85%) as a colorless crystal.

Provenance & Evidence