1,1'-Carbonyldiimidazole → 6-Chloro-3-(4-chloro-2-thenoyl)-2-oxindole-1-carboxamide

Participants

Reaction Steps

The experimental procedure used to produce the title compound was adopted from Example 55. A 463 mg (2.85 mmole) portion of 4-chloro-2-thiophenecarboxylic acid (prepared according to Iriarte, J., et al., J. Het. Chem., 13, 393 (1976)) was transformed into the acyl imidazole by reaction with 500 mg (3.09 mmole) of to 1,1'-carbonyldiimidazole. The intermediate 4-chloro-2-thiophene-(l-imidazo)carboxamide coupled directly with 500 mg (2.37 mmole) of 6-chloro-2-oxindole-1-carboxamide in the presence of 783 mg (6.41 mmole) of 4-(N,N-dimethylamino)pyridine to give 665 mg of crude greenish-yellow solid. Recrystallization gave 450 mg (1.27 mmole, 53% yield) of pure title compound as a yellow solid, m.p. 231°-3° C. (acetic acid).

Provenance & Evidence