Benzoyl chloride, 3,4,5-trimethoxy- → N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamide

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Reaction Steps

A procedure similar to that in Example 4 was used. 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1 and 3,4,5-trimethoxy-benzoyl chloride prepared in the step 1 were used as starting materials, allowed to react at room temperature overnight, followed by post-treatment to obtain a crude product, which was purified by a silica gel column chromatography eluted with a gradient of dichloromethane and ethyl acetate (100:0-10:1) to obtain a product as a white solid in a yield of 61.7%, mp: 157-158 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.75 (6H, s, 2×OCH3), 3.77 (3H, s, OCH3), 3.87 (3H, s, OCH3), 4.21 (2H, s, CH2), 6.75 (2H, d, J=8.96 Hz, ArH), 6.92 (2H, s, ArH), 7.23˜7.35 (7H, m, ArH), 11.72 (1H, br, CONH); EI-MS m/e (%): 490.3 (M, 82), 195.1 (100); HREI-MS Calcd. for C27H26N2O5S: 490.1562. found: 490.1560.

Provenance & Evidence