Pyrazole → 4,4,5,8-Tetramethyl-6-(1-ethyl-5-ethanesulfonyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide

HRID 1069

Reaktionsgleichung

Reaktionsgleichung von HRID 1069
[CH3:1][C:2]1([CH3:26])[C:11]2[C:6](=[C:7]([CH3:23])[CH:8]=[C:9]([C:13]([C:15]3[CH:16]=[N:17][N:18]([CH2:21][CH3:22])[C:19]=3[OH:20])=[O:14])[C:10]=2[CH3:12])[S:5](=[O:25])(=[O:24])[CH2:4][CH2:3]1.N1C=CC=N1.C(=O)([O-])[O-].[K+].[K+].[CH2:38]([S:40](Cl)(=[O:42])=[O:41])[CH3:39]>C(Cl)Cl.O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH3:26][C:2]1([CH3:1])[C:11]2[C:6](=[C:7]([CH3:23])[CH:8]=[C:9]([C:13]([C:15]3[CH:16]=[N:17][N:18]([CH2:21][CH3:22])[C:19]=3[O:20][S:40]([CH2:38][CH3:39])(=[O:42])=[O:41])=[O:14])[C:10]=2[CH3:12])[S:5](=[O:25])(=[O:24])[CH2:4][CH2:3]1

Komponenten

8

Edukt 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 11667Ethanesulfonyl chlorideHCID 178418286HCID 178418286, Verbindung

Produkt 1

HCID 154773584,4,5,8-Tetramethyl-6-(1-ethyl-5-ethanesulfonyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.7 Gram (1.9 mmol) of the 4,4,5,8-tetramethyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound Ic-1) corresponding to pyrazole derivative (I-H), obtained in Referential Production Example 5, was dissolved in 8 ml of methylene chloride. Then, a solution of 0.51 g (3.8 mmol) of potassium carbonate in 5 ml of water was added, and further, 0.49 g (3.8 mmol) of ethanesulfonyl chloride and 0.05 g (0.2 mmol) of benzyltriethylammonium chloride, corresponding to compound B-A-Hal, were added. The mixture was allowed to react at room temperature for 2 hours, and further refluxed under heat for 2 hours. The reaction mixture was allowed to cool, and then a methylene chloride layer was recovered and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant oil was purified by silica gel column chromatography to give 0.73 g (yield 82%) of 4,4,5,8-tetramethyl-6-(1-ethyl-5-ethanesulfonyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound Ic-2).

Aufarbeitung

  1. customto react at room temperature for 2 hours
  2. temperaturefurther refluxed
  3. temperatureunder heat for 2 hours
  4. temperatureto cool
  5. customa methylene chloride layer was recovered
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resultant oil was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b437e05b173c435b946ece88305eb18d
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723408

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