反応 #2286374
ord-ac5a5ecda3dc4cfda13571153c50f3c1
反応方程式
反応物
試薬
反応条件
後処理
- 1温度The reaction mixture was cooled to room temperature
- 2温度heated to 35° C. under nitrogen for 2 h
- 3温度The reaction mixture was cooled
- 4濃縮concentrated under reduced pressure
- 5workup.DISSOLUTIONThe residue was redissolved in dichloromethane (80 mL)
- 6洗浄washed with water (70 mL)
- 7抽出The aqueous layer was re-extracted with methylene chloride (100 mL)
- 8洗浄The combined organic layers were washed with water (50 mL) and brine (50 mL)
- 9乾燥dried over sodium sulfate
- 10ろ過filtered
- 11濃縮concentrated under reduced pressure
- 12その他purified
- 13洗浄The product eluted with a gradient of acetonitrile in water
実験手順
A suspension of 2,2,2-trifluoro-N-methyl-N-(2-pyridin-3-yl-thiazol-5-yl)-acetamide (1.0 g, 3.5 mmol) and N-chlorosuccinimide (0.557 g, 4.2 mmol) in acetonitrile (30 mL) was heated to 63° C. under nitrogen for 3 h. The reaction mixture was cooled to room temperature and it was treated with additional N-chlorosuccinimide (0.557 g, 4.2 mmol) and heated to 35° C. under nitrogen for 2 h. The reaction mixture was cooled and concentrated under reduced pressure. The residue was redissolved in dichloromethane (80 mL) and washed with water (70 mL). The aqueous layer was re-extracted with methylene chloride (100 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over sodium sulfate, filtered, concentrated under reduced pressure and purified using reverse phase chromatography. The product eluted with a gradient of acetonitrile in water. The desired product was isolated as a thick brown gum (0.337 g, 30%): 1H NMR (400 MHz, CDCl3) δ 9.12 (br, 1H), 8.75 (br, 1H), 8.22 (d, J=7.9 Hz, 1H), 7.28 (br, 1H), 3.40 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −69.3; ESIMS m/z 324.3 (M+2); IR (thin film) 1772 cm−1.