Pyridine → p-Toluenesulfonamide, N-benzyl-

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Reaction Steps

To a suspension of P-HOBT 6 (1.01 g, 0.49 mmol) in CH2Cl2 (5 mL) was added p-toluenesulfonyl chloride (0.280 g, 1.47 mmol, 3.00 equiv.) and pyridine (0.155 g, 0.160 mL, 1.98 mmol, 4.04 equiv.). The suspension was subsequently rocked for 60 minutes at 25° C. The polymer was then filtered and washed with CH2Cl2 (3×5 mL), MeCN (3×5 mL), and MeOH (3×5 mL). The polymer was re-suspended in CH2Cl2 (5 mL), followed by the addition of benzylamine (0.026 g, 0.027 mL, 0.24 mmol, 0.49 equiv. based on P-HOBT 6). The suspension was rocked at 25° C. for 2 h. The polymer was then filtered and washed with CH2Cl2 (2×5 mL). The filtrate and washings were combined and concentrated to yield 0.050 g (77%) of N-benzyl-p-toluenesulfonamide as a light yellow crystalline solid.

Provenance & Evidence