Acetic Acid → HCID 53912360, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-[3-(2-ethoxycarbonylbenzoyl)phenyl]- 3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxamide (4.4 g) and potassium hydroxide pellets (1.8 g) in a mixture of ethanol (100 cc) and distilled water (50 cc) is stirred at a temperature in the vicinity of 20° C. for 3 hours. The solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C. The residue is dissolved in distilled water (350 cc) and the solution obtained is adjusted to a pH in the region of 4 by adding an aqueous 4N acetic acid solution. The crystals formed are separated by filtration, washed 5 times with distilled water (500 cc in total) and dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 20° C. in the presence of potassium hydroxide pellets. A crude product (3.5 g) is thereby obtained, which is dissolved in a boiling mixture (200 cc) of butan-1-ol and dimethylformamide (35:65 by volume). Decolourizing charcoal (0.5 g) is added to the solution obtained and the suspension is filtered in the heated state. The filtrate is cooled at a temperature in the vicinity of 4° C. for 3 days. The crystals formed are separated by filtration, washed 3 times with a mixture (30 cc in total) of butan-1-ol and dimethylformamide (35:65 by volume), 3 times with ethanol (90 cc in total) and 3 times with diethyl ether (90 cc in total) and then dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 20° C. in the presence of potassium hydroxide pellets. N-[3-(2-carboxybenzoyl) phenyl]-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxamide (1.8 g) in the form of white crystals, m.p. 315° C. is thereby obtained.

Provenance & Evidence