Triethylamine → 2-(2-Methoxybenzamido)-4-methylthiophene-3-carboxamide

Participants

Reaction Steps

A solution of 2-amino-4-methylthiophene-3-carboxamide (0.47 g, 3 mmol), Et3N (0.46 mL, 3.3 mmol), and dimethylaminopyridine (0.073 g, 0.64 mmol) in CH2Cl2 (10.0 mL) was cooled in an ice bath, and 2-methoxybenzoyl chloride (513 mg, 3.0 mmol) was added dropwise to this mixture. The reaction was stirred for 1 h, and water (20 mL) was added. The insoluble solids were filtered, and the layers were separated. The organic layer was dried and the solvent removed under vacuum to give a residue which was purified with silica gel using EtOAc-hexanes to give 2-(2-methoxybenzamido)-4-methylthiophene-3-carboxamide (0.38 g, 44% yield). LC/MS: m/z 291.1 (M+H)+ at 2.59 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Provenance & Evidence