3-(Methylthio)propylamine → 2-amino-3-iodo-N-(3-(methylthio)propyl)benzamide

Participants

Reaction Steps

To a 100-mL round-bottomed flask was added 2-amino-3-iodobenzoic acid (1.50 g, 5.70 mmol, Bosche Scientific) and 3-(methylthio)propylamine (0.72 mL, 6.84 mmol, Acros) in EtOAc (15 mL) followed by DIEA (1.19 mL, 6.84 mmol) and 1-propanephosphonic acid cyclic anhydride (3.99 mL, 6.27 mmol, 50% in EtOAc, Sigma Aldrich). The reaction was stirred at RT for 4 h, and then quenched with sat. NaHCO3. The layers were separated and the organic layer was washed with sat. NaHCO3, brine, then dried (MgSO4), filtered and concentrated to give the crude product. MS (ESI, pos. ion) m/z: 350.9 (M+1); 1H NMR (400 MHz, CDCl3) δ ppm 7.74 (1H, dd, J=7.6, 1.4 Hz), 7.30 (1H, dd, J=7.8, 1.4 Hz), 6.41 (1H, t, J=7.8 Hz), 6.32 (1H, br. s.), 3.54 (2H, q, J=6.7 Hz), 2.61 (2H, t, J=6.9 Hz), 2.09-2.17 (3H, m), 1.92 (2H, quin, J=6.8 Hz)

Provenance & Evidence