Реакция #1379684

Уравнение реакции

4-Methoxy-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl) carbonylthiochroman-1,1-dioxide

potassium carbonate

p-nitrobenzenesulfonyl chloride

chlorobenzyltriethylammonium chloride

→

4-methoxy-5-methyl-6-(1-ethyl-5-(p-nitrobenzenesulfonyl) oxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide

Выход 70.0%

Растворители

methylene chloride

water

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added
2. 2
   Другоеto react at room temperature for 2 hours
3. 3
   ТемператураFurther, the reaction mixture was refluxed
4. 4
   Температураunder heat for 2 hours
5. 5
   Температураto cool
6. 6
   Другоеits methylene chloride layer was separated
7. 7
   Сушкаdried over anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONThen, the solvent was distilled off under reduced pressure
9. 9
   Другоеthe resultant oil was purified
10. 10
    Другоеwith flush column chromatography

Методика

4-Methoxy-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl) carbonylthiochroman-1,1-dioxide was used as a starting material (XIH). And, 0.4 g (1.10 mmol) thereof was dissolved in 6 ml of methylene chloride, a solution of 0.30 g (2.20 mmol) of potassium carbonate as a base in 4 ml of water was added, and 0.29 g (1.30 mmol) of p-nitrobenzenesulfonyl chloride and 0.05 g (0.2 mmol) of chlorobenzyltriethylammonium chloride as reaction reagents (XII) were added. The resultant mixture was allowed to react at room temperature for 2 hours. Further, the reaction mixture was refluxed under heat for 2 hours. After the reaction mixture was allowed to cool, its methylene chloride layer was separated, and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the resultant oil was purified with flush column chromatography to give 0.42 g (yield 70%) of 4-methoxy-5-methyl-6-(1-ethyl-5-(p-nitrobenzenesulfonyl) oxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound No. 13) as an end compound which comes under the general formula (XI). Table 22 shows the structures of the starting material (XIH) and the reaction reagent (XII), and the structure and the yield of the end product (XI).

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