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Nitrile to Amide



Example 1

To a stirred solution of urea hydrogen peroxide (4.2 g, 43.8 mmol) in H2O (12 mL) was added NaOH (1.04 g, 25.5 mmol). The resulting mixture was cooled in an ice bath before a solution of the SM (1.00 g, 7.29 mmol) in EtOH (5 mL) was added. The reaction mixture was stirred vigorously at RT for 2 h. The mixture was diluted with H2O (100 mL) and EtOAc (100 mL) and was stirred 5 min, after which time 1M HCl was until pH 4. The layers were separated and the aq layer was further extracted with EtOAc (3 x 100 mL). The combined organics were dried (MgSO4) and concentrated to give a white solid. The solid was triturated with 2:1 ether/heptane (90 mL) for 1 h, before filtering to provide the product as a white solid. [1.05 g]

[Patent Reference: WO2012069948, page 63, (3.9 MB)]