反应详情

A 0.78 g (4.59 nmuoles) sample of 4-acetyl-2-thio-phenecarboxylic acid (prepared according to Satonaka, H., Bull. Chem. Soc. Japan 56:2463 (1983)) was combined with 0.95 g (5.85 mmoles) of 1,1'-carbonyldiimidazole in 10 ml of N,N-dimethylformamide and stirred at room temperature under argon atmosphere. After two hours the reaction contents were transferred to an addition funnel and slowly added to a slurry of 0.88 g (4.18 mmoles) of 5-chloro-2-oxindole-1-carboxamide and 1.38 g (11.28 mmoles) of 4-(N,N-dimethylamino)pyridine in 30 ml of N,N-dimethylformamide stirring at 5° C. (ice bath) under an inert atmosphere. The reaction contents were stirred for fifteen minutes at 5° C. after complete addition followed by twenty-four hours at room temperature. Pouring the reaction mixture into 110 ml of 0.3N hydrochloric acid cause the precipitation of a greenish-yellow solid. Filtration followed by sequential washing with 3N hydrochloric acid and water, provided the crude product which was recrystallized twice from acetic acid to give 0.34 g (0.94 mmoles, 22% yield) of pure 5-chloro-3-(4-acetyl-2-thenoyl)-2-oxindole-1-carboxamide as a greenish-yellow solvated complex with 0.2 equivalents of acetic acid, m.p. 230-233° C.

1. customAfter two hours the reaction contents
2. customwere transferred to an addition funnel
3. customThe reaction contents
4. stirringwere stirred for fifteen minutes at 5° C.
5. additionafter complete addition
6. waitfollowed by twenty-four hours at room temperature
7. customthe precipitation of a greenish-yellow solid
8. filtrationFiltration
9. washby sequential washing with 3N hydrochloric acid and water
10. customprovided the crude product which
11. customwas recrystallized twice from acetic acid