Benzoyl chloride → HCID 57991578, compound

Participants

Reaction Steps

To a 100 ml three-necked flask were added 0.50 g (1.69 mmol) 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1, 1.42 g (10.12 mmol) triethylamine and 40 ml ethyl acetate, and then added dropwise 0.48 g (3.38 mmol) benzoyl chloride dissolved in 10 ml ethyl acetate. The resulting mixture was magnetically stirred overnight at room temperature, filtrated, washed with ethyl acetate, the filtrate was washed with 1N aqueous sodium hydroxide solution, then washed with water until neutrality, dried over anhydrous sodium sulfate, filtered and concentrated under a reduced pressure to give a crude product, which was subjected to a silica gel column chromatography eluted with petroleum ether/ethyl acetate (5:1) to obtain a 0.39 g product as a white solid in a yield of 57.4%, mp: 146-147 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.88 (3H, s, OCH3), 4.20 (2H, s, CH2), 7.01 (2H, d, J=8.72 Hz, ArH), 7.31 (2H, d, J=8.72 Hz, ArH), 7.42˜7.65 (7H, m, 6ArH+CONH), 8.09 (2H, d, J=7.28 Hz, ArH), 8.17 (2H, d, J=7.28 Hz, ArH); EI-MS m/e (%): 400.0 (M+, 94), 104.9 (100); HREI-MS Calcd. for C24H20N2O2S: 400.1245. found: 400.1235.

Provenance & Evidence