2-Methoxybenzoyl chloride → N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-2-methoxy-benzamide

Participants

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 o-methoxybenzoyl 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 65.6%, mp: 147-148└. 1H-NMR (CDCl3, 400 MHz) δ: 3.84 (3H, s, OCH3), 4.09 (3H, s, OCH3), 4.21 (2H, s, CH2), 6.97 (2H, d, J=8.68 Hz, ArH), 7.05 (1H, d, J=8.12 Hz, ArH), 7.14 (1H, t, J=8.12 Hz, ArH), 7.22˜7.32 (5H, m, ArH), 7.53˜7.56 (3H, m, ArH), 8.28 (1H, dd, J=7.84 Hz, 1.68 Hz, ArH), 11.05 (1H, br, CONH); EI-MS m/e (%): 430.2 (M+, 89), 135.1 (100); HREI-MS Calcd. for C25H22N2O3S: 430.1351. found: 430.1357.

Provenance & Evidence