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

Participants

Reaction Steps

A procedure similar to that in Example 4 was used. 4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine prepared in Example 6 and p-fluorobenzoyl chloride were used as starting materials, allowed to react at 35-40° C. for 48 hours, followed by post-treatment to obtain a crude product, which was purified by a silica gel column chromatography eluted with petroleum ether and ethyl acetate (4:1) to obtain a product as a yellow solid in a yield of 81.3%, mp: 188-189 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.82 (3H, s, OCH3), 4.33 (2H, s, CH2), 6.87 (2H, d, J=8.68 Hz, ArH), 7.10 (2H, t, 3JFH=3JHH=8.68 Hz, ArH), 7.37 (2H, d, J=8.40 Hz, ArH), 7.39 (2H, d, J=8.68 Hz, ArH), 7.89 (2H, dd, 3JHH=8.68, 4JFH=5.02 Hz, ArH), 8.19 (2H, d, J=8.68 Hz, ArH); EI-MS m/e (%): 463.1 (M+, 60), 123.0 (100); HREI-MS Calcd. for C24H18FN3O4S: 463.1002. found: 463.1000. Anal. Calcd. for C24H18FN3O4S: C, 62.19; H, 3.91; N, 9.07. found: C, 62.21; H, 3.82; N, 9.02.

Provenance & Evidence