Acetic Anhydride → HCID 178522951, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(4-chlorobenzyl)-3-(2-chloro-5-(morpholin-4-ylmethyl)thien-3-yl)-3-oxopropanamide (Preparation 20, 20.0 g), triethylorthoformate (15.4 mL), and acetic anhydride (15.4 mL) is heated to 150° C. with removal of the distillate with a Dean-Stark trap. After 3 h, the volatiles are removed at 40 Torr (50° C.) and then at 0.2 Torr (100° C.) for 1 h to afford a brown oil. A portion of this residue (10.0 g) is dissolved in ethanol (150 mL) and N-aminoethylmorpholine (4.1 g) is added. The mixture is stirred at room temperature for 24 h and then is concentrated in vacuo. The crude product is purified by column chromatography (CH2Cl2/methanol, 97/3) to afford 4.28 g of the title compound as a brown oil. Physical characteristics. 1H NMR (300 MHz, DMSO-d6) δ 10.51, 9.89, 7.62, 7.58, 7.37, 6.92, 4.44, 3.62, 3.58, 3.47, 3.40, 2.42, 2.32.

Provenance & Evidence