4-Cyanobenzoyl chloride → 4-cyano-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-cyanobenzoyl chloride prepared in the step 1 of Example 13 were used as starting materials, allowed to react at room temperature overnight, followed by post-treatment to obtain a crude product, which was recrystallized with a solvent mixture of ethyl acetate and petroleum ether to obtain a product as a off-white solid in a yield of 62.9%, mp: 244-245└. 1H-NMR (CDCl3, 400 MHz) δ: 4.33 (2H, s, CH2), 7.07 (2H, t, 3JFH=3JHH=8.44 Hz, ArH), 7.38 (2H, d, J=8.40 Hz, ArH), 7.43 (2H, dd, 3JHH=8.72, 4JFH=5.32 Hz, ArH), 7.75 (2H, d, J=7.84 Hz, ArH), 7.98 (2H, d, J=8.12 Hz, ArH), 8.20 (2H, d, J=8.40 Hz, ArH); EI-MS m/e (%): 458.3 (M+, 79), 129.9 (100); HREI-MS Calcd. for C24H15FN4O3S: 458.0849. found: 458.0850. Anal. Calcd. for C24H15FN4O3S: C, 62.88; H, 3.30; N, 12.22. found: C, 62.52; H, 2.96; N, 12.04.

Provenance & Evidence