反应详情

To a cold (0° C.) solution of 4-(4-bromophenyl)-2-(2-cyano-acetylamino)-thiophene-3-carboxylic acid ethyl ester (4.0 g, 10.18 mmol) in methylene chloride (34 mL) was added sulfuryl chloride (0.82 mL, 10.2 mmol). The cold bath was removed, and the reaction was stirred at room temperature for 4 h. Saturated aqueous sodium bicarbonate solution was then added (30 mL) to the reaction. The layers were separated, and the aqueous was extracted with additional methylene chloride (3×15 mL). The combined organic layers were dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give the titled compound as a solid. MS (DCI/NH3) m/e 446 (M+NH3)+, NMR (300 MHz, CDCl3): δ ppm 12.1 (br s, 1H), 7.53 d, 2H), 7.09 (d, 2H), 4.08 (q, 2H), 3.67 (s, 2H), and 0.91 (t, 3H).

1. customThe cold bath was removed
2. additionSaturated aqueous sodium bicarbonate solution was then added (30 mL)
3. customto the reaction
4. customThe layers were separated
5. extractionthe aqueous was extracted with additional methylene chloride (3×15 mL)
6. dry with materialThe combined organic layers were dried with anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure