Reacción #1379684

Ecuación de reacción

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

Rendimiento 70.0%

Disolventes

methylene chloride

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   Otroto react at room temperature for 2 hours
3. 3
   TemperaturaFurther, the reaction mixture was refluxed
4. 4
   Temperaturaunder heat for 2 hours
5. 5
   Temperaturato cool
6. 6
   Otroits methylene chloride layer was separated
7. 7
   Secadodried over anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONThen, the solvent was distilled off under reduced pressure
9. 9
   Otrothe resultant oil was purified
10. 10
    Otrowith flush column chromatography

Procedimiento

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).

Fuente