N-tert-butyl-2-chlorobenzamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The mixture of 2-chlorobenzoic acid (20 g, 128 mmol), HOBT (34.6 g, 256 mmol), EDCI (48.8 g, 256 mmol), 2-methylpropan-2-amine (9.3 g, 128 mmol) and TEA (25.9 g, 256 mmol) in THF (600 mL) was stirred at room temperature overnight. After solvent evaporation, the mixture was diluted with ethyl acetate (600 mL) and washed with water (3×300 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc/PE (1:5) to give the title product as a white solid (23.9 g, yield: 88.5%). LC-MS: m/e=212 (M+H)+; Rt=0.85 min. After solvent evaporation the mixture was diluted with ethyl acetate (600 mL) washed with water (3×300 mL) The organic layer was dried over Na2SO4 filtered concentrated The residue was purified by column chromatography on silica gel eluting with EtOAc/PE (1:5)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The mixture of 2-chlorobenzoic acid (20 g, 128 mmol), HOBT (34.6 g, 256 mmol), EDCI (48.8 g, 256 mmol), 2-methylpropan-2-amine (9.3 g, 128 mmol) and TEA (25.9 g, 256 mmol) in THF (600 mL) was stirred at room temperature overnight. After solvent evaporation, the mixture was diluted with ethyl acetate (600 mL) and washed with water (3×300 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc/PE (1:5) to give the title product as a white solid (23.9 g, yield: 88.5%). LC-MS: m/e=212 (M+H)+; Rt=0.85 min. After solvent evaporation the mixture was diluted with ethyl acetate (600 mL) washed with water (3×300 mL) The organic layer was dried over Na2SO4 filtered concentrated The residue was purified by column chromatography on silica gel eluting with EtOAc/PE (1:5)