Boron tribromide → N-[5-cyclohexylmethyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4-dihydroxy-benzamide

Participants

Reaction Steps

A procedure similar to that in Example 7 was used. N-[5-cyclohexylmethyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,4-dimethoxy-benzamide prepared in Example 48 and boron tribromide were used as starting materials. The obtained crude product was recrystallized with ethyl acetate to obtain a product as a white solid in a yield of 60.5%, mp: 133-134 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 0.75˜0.90 (2H, m), 0.95˜1.18 (3H, m), 1.15˜1.17 (6H, m), 2.65 (2H, d, J=7.0 Hz), 6.75 (1H, d, J=8.0 Hz, ArH), 6.76 (2H, d, J=8.4 Hz, ArH), 7.32 (2H, d, J=8.4 Hz, ArH), 7.41 (1H, d, J=2.4 Hz, ArH), 7.46 (1H, dd, J=8.4, 2.4 Hz, ArH), 9.52 (1H, br, OH), 12.15 (1H, br, CONH); EI-MS m/e (%): 424.1 (M+, 21), 288.1 (36), 205.1 (100); HREI-MS Calcd. for C23H24N2O4S: 424.1457. found: 424.1458.

Provenance & Evidence