1,1'-Carbonyldiimidazole → 4-Nitro-N-(2-hydroxy-2-methyl-propyl)-3,5-dimethyl-benzamide

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Reaction Steps

3,5-Dimethyl-4-nitrobenzoic acid (1 g, 5.12 mmol) is suspended in dry tetrahydrofuran (10 mL) and 1,1′-carbonyldiimidazole (0.91 g, 5.64 mmol) is added. The mixture is stirred for 3 hours then 1-amino-2-methyl-propan-2-ol (patent WO2010/84767, 1 g, 11.22 mmol) is added and the mixture stirred for 30 minutes. The solvent is removed, the residue suspended in EtOAc and washed with 0.2 M aqueous HCl solution, saturated sodium bicarbonate solution and brine, dried and the solvent removed under vacuum to give the title compound (Yield 1.2 g).

Provenance & Evidence