반응 #1379684

ord-f466f0ba3e8f4966a881aa268c7a4419

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.ADDITIONwere added
  2. 2
    기타to react at room temperature for 2 hours
  3. 3
    온도Further, the reaction mixture was refluxed
  4. 4
    온도under heat for 2 hours
  5. 5
    온도to cool
  6. 6
    기타its methylene chloride layer was separated
  7. 7
    건조dried over anhydrous sodium sulfate
  8. 8
    workup.DISTILLATIONThen, the solvent was distilled off under reduced pressure
  9. 9
    기타the resultant oil was purified
  10. 10
    기타with flush column chromatography

실험 절차

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).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05756759uspto-grants-1998_05