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

Participants

Reaction Steps

A procedure similar to that in Example 4 was used. 4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine prepared in Example 9 and p-fluorobenzoyl chloride were used as starting materials, allowed to react at 35-40° C. for 24 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 pale yellow solid in a yield of 69.6%, mp: 120-122 └. 1H-NMR (CDCl3, 400 MHz) δ: 4.33 (2H, s, CH2), 7.12 (2H, t, 3JFH=3JHH=8.44 Hz, ArH), 7.18 (2H, t, 3JFH=3JHH=8.40 Hz, ArH), 7.38 (2H, d, J=8.68 Hz, ArH), 7.49 (2H, dd, 3JHH=8.72, 4JFH=5.32 Hz, ArH), 7.99 (2H, dd, 3JHH=8.96, 4JFH=5.32 Hz, ArH); 8.20 (2H, d, J=8.68 Hz, ArH); EI-MS m/e (%): 451.0 (M+, 32), 123.0 (100); HREI-MS Calcd. for C23H15F2N3O3S: 451.0802. found: 451.0818. Anal. Calcd. for C23H15F2N3O3S: C, 61.19; H, 3.35; N, 9.31. found: C, 61.16; H, 3.08; N, 9.35.

Provenance & Evidence